[ CAS No. 162537-11-3 ] {[proInfo.proName]}

Name: 162537-11-3|(S)-2-((Methoxycarbonyl)amino)-3,3-dimethylbutanoic acid|97%
Brand: Ambeed
SKU: A393007
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2D 3D

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Quality Control of [ 162537-11-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 162537-11-3 ]

SDS Specification

Alternatived Products of [ 162537-11-3 ]

Product Details of [ 162537-11-3 ]

CAS No. :	162537-11-3	MDL No. :	MFCD07778455
Formula :	C₈H₁₅NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NWPRXAIYBULIEI-RXMQYKEDSA-N
M.W :	189.21	Pubchem ID :	11263950
Synonyms :		Chemical Name :	(S)-2-((Methoxycarbonyl)amino)-3,3-dimethylbutanoic acid

Calculated chemistry of [ 162537-11-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.56
TPSA :	75.63 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	1.3
Log Po/w (WLOGP) :	0.84
Log Po/w (MLOGP) :	0.51
Log Po/w (SILICOS-IT) :	-0.17
Consensus Log Po/w :	0.8

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.5
Solubility :	5.95 mg/ml ; 0.0315 mol/l
Class :	Very soluble
Log S (Ali) :	-2.49
Solubility :	0.614 mg/ml ; 0.00325 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.64
Solubility :	43.0 mg/ml ; 0.228 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.36

Safety of [ 162537-11-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 162537-11-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 162537-11-3 ]
Downstream synthetic route of [ 162537-11-3 ]

[ 162537-11-3 ] Synthesis Path-Upstream 1~2

1
[ 20859-02-3 ]
[ 79-22-1 ]
[ 162537-11-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide In 1,4-dioxane; water at 60℃; for 18 h;	Step 1: Synthesis of (S)-2-(methoxycarbonylaniino)-3,3-dimethylb tanoic acid:A stirred solution of (S)-2-amino-3,3-dimethylbutanoic acid (about 5.0 g, 38. 16 mmol) in Dioxane (about 20 ml) and sodium hydroxide (2N, 62 ml, P^H = 8-9) at about 0 °C, methychlroformate (about 5.88 ml, 76.33 mmol) was added drop wise and stirred at about 60 °C for about 18 hours. The reaction mixture was cooled to room temperature, extracted with DCM, the aqueous layer was separated and acidified with I N HCl. The resulting solution was extracted with EtOAc, dried over Na₂S0₄ and the solvent was evaporated under reduced pressure. The resulting crude was stirred in hexane and decants to afford the title compound as a solid. Wt: 8.5 g: Yield: quantitative; NMR (300 MHZ, CDCI₃): δ 5.25 (d, 1 H, J = 10.5 Hz), 4. 19(d, 1 H, J = 9.6 Hz) 3.70 (s, 3H), 1 .03 (s, 9H); Mass: [M- l ]^' 188 ( 100percent); IR ( Br, cm ¹ ): 3379, 2974, 1727, 1688, 1546, 1466, 1332, 1263. 121 1 , 1070, 1034, 1018, 843, 696.
98%	With sodium hydroxide In 1,4-dioxane; water at 25 - 60℃; for 22 h;	Example 1; methyl (1S)-1-( (12- [ (2S, 3S)-3-amino-2-hydroxy-4-phenylbutyl]-2- [4- (2- pyridinyl) benzyl] hydrazino} carbonyl)-2, 2-dimethylpropylcarbamate; Example 1A; (2S)-2-[(methoxycarbonyl) amino] -3,3-dimethylbutanoic acid; (L)-tert-Leucine (10 g, 0.076 mol) was dissolved in 1,4-dioxane (40 mL) and treated with 2M NaOH (125 mL, 3.2 equivalents) followed by dropwise addition of methyl chlorofonnate (11.2 mL, 1.9 equivalents) at 25°C. The mixture was heated at 60°C for 22 hrs, cooled, and extracted twice with dichloromethane. The aqueous layer was separated, cooled in ice bath, and acidified with 4N HC1 (60 mL). The mixture was extracted three times with ethyl acetate, and the organic layer was separated, dried with sodium sulfate, filtered, and the solvents were evaporated to give 14.1 g (98percent) of the title compound
98%	Stage #1: With sodium hydroxide In 1,4-dioxane; water at 25 - 60℃; for 22 h; Stage #2: With hydrogenchloride In water	EXAMPLE 1A (2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoic Acid (L)-tert-Leucine (10 g, 0.076 mol) was dissolved in 1,4-dioxane (40 mL) and treated with 2M NaOH (125 mL, 3.2 equivalents) followed by dropwise addition of methyl chloroformate (11.2 mL, 1.9 equivalents) at 25° C. The mixture was heated at 60° C. for 22 hrs, cooled, and extracted twice with dichloromethane. The aqueous layer was separated, cooled in ice bath, and acidified with 4N HCl (60 mL). The mixture was extracted three times with ethyl acetate, and the organic layer was separated, dried with sodium sulfate, filtered, and the solvents were evaporated to give 14.1 g (98percent) of the title compound.

98%	With sodium hydroxide In water at 25℃; for 2 h;	Example 1 A 15percent by weight sodium hydroxide aqueous solution was added to the aqueous solution (72.4 g) containing L-tert-leucine (13.2 g, 0.10 mol), to adjust the pH to 13.0. Then, methyl chloroformate (9.52 g, 0.10 mol, 1.00 equivalent) was slowly added thereto with maintaining the temperature of the mixture below 25°C. At the time, the pH was decreased by adding methyl chloroformate; however, the pH of the solution was maintained at 10.0-12.8 by simultaneously adding a 15percent by weight of sodium hydroxide aqueous solution. After the addition of methyl chloroformate, the mixture was stirred for 2 hours. Then, the yield and quality were analyzed by HPLC. Yield: 98percent, Reaction selectivity: 100percent
92%	Stage #1: With sodium hydroxide In 1,4-dioxane; water at 50 - 60℃; for 18 h; Stage #2: With hydrogenchloride In 1,4-dioxane; water at 0℃;	A solution of L-tert-Leucine (25 g, 190.58 mmol) in a mixture of dioxane (100 mL) and aqueous NaOH solution (315 mL, 2N) was treated dropwise with methyl chloroformate (29.3 mL, 379.19 mmol), keeping the internal temperature below 50° C. The mixture was warmed to 60° C. and stirred for 18 hours, cooled to 25° C. and extracted with dichloromethane. The aqueous phase was cooled to 0° C. and the pH was adjusted to about 1-2 with concentrated HCl. The mixture was partitioned between ethyl acetate and water. The combined organic extracts were washed with brine, dried over MgSO₄, filtered and concentrated. A solution of the concentrate in ether was treated with hexanes to afford the crystalline product (33.22 g, 92percent yield), which was collected by filtration.
92%	Stage #1: With sodium hydroxide In 1,4-dioxane; water at 50 - 60℃; for 18 h; Stage #2: With hydrogenchloride In water at 0℃;	EXAMPLE 1F (2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoic acid A solution of L-tert-Leucine (25 g, 190.58 mmol) in a mixture of dioxane (100 mL) and aqueous NaOH solution (315 mL, 2N) was treated dropwise with methyl chloroformate (29.3 mL, 379.19 mmol), keeping the internal temperature below 50° C. The mixture was warmed to 60° C. and stirred for 18 hours, cooled to 25° C. and extracted with dichloromethane. The aqueous phase was cooled to 0° C. and the pH was adjusted to about 1-2 with concentrated HCl. The mixture was partitioned between ethyl acetate and water. The combined organic extracts were washed with brine, dried over MgSO₄, filtered and concentrated. A solution of the concentrate in ether was treated with hexanes to afford the crystalline product (33.22 g, 92percent yield), which was collected by filtration.
89%	at 60℃; for 20 h;	2-Methoxycarbonylamino-3,3-dimethyl-butyric acid (3) (0136) Into a 250 mL flask was placed L-tert-Leucine (5.0 gm, 38 mmol), 2N NaOH (66 mL), and methyl chloroformate (5.86 mL, 76 mmol, 2.0 equivalents). The reaction mixture was heated to 60° C., turning light-yellow. After approximately 20 hours, the heat was removed and the mixture cooled to room temperature, and then to 0° C. The reaction mixture was quenched at 0° C. with 2 N HCl (40 mL) to pH 1. The acidified mixture was transferred to a separatory funnel and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with water (2×150 mL), and saturated NaCl (150 mL), and then dried over Na₂SO₄. The organic layer was filtered and concentrated under reduced pressure to give a clear oil. The oil was azeotroped with toluene (3×50 mL), and then dried under high vacuum to give 6.4 gm (89percent) of 3 as a white solid. ¹H NMR (DMSO) δ 12.51 (bs, 1H), 7.28 (d, 1H), 3.80 (d, 1H), 3.53 (s, 3H), 0.93 (s, 9H); MS (M)⁺=190; HPLC t_R2.8 minutes.
76%	Stage #1: With sodium hydroxide In 1,4-dioxane; water at 20 - 60℃; for 20 h; Stage #2: With hydrogenchloride In 1,3-dioxane; water	Compound 1; L-tert-leucine (12.251 g, 93.4 mmol) was dissolved in a mixture of NaOH (2N, 154 mL) and dioxane (50.5 mL). Methyl chloroformate (14.30 mL, 185.84 mmol) was added slowly (e.g., dropwise) to the solution at room temperature ("r.t."). The resulting reaction mixture was heated to 60⁰C and stirred for 20 <n="454"/>hours ("h"). The reaction mixture was cooled to r.t. and washed with dichloromethane ("DCM.") The aqueous layer was acidified to pH 2 using concentrated HCl. The aqueous layer was then extracted with ethyl acetate, and the combined organic layers were dried over Na₂SO₄, and concentrated. The resulting oil was crystallized from hexane to give Compound 1 as a white solid (13.354 g, 70.6 mmol, 76percent). TLC R_f (silica gel 60 plate, methanol /EXTM, 1:19) = 0.78.
71%	With sodium carbonate; sodium hydroxide In water at 20℃; for 3.25 h; Cooling with ice	General procedure: Na₂CO₃ (276mg, 2.6mmol) was added to aq NaOH (5mL of 1M/H₂O, 5mmol) solution of d-valine (586mg, 5.00mmol) and the resulting solution was cooled with ice-water bath. Methyl chloroformate (0.420mL, 5.40mmol) was added dropwise, the cooling bath was removed and the reaction mixture was stirred at ambient temperature for 3.25h. The reaction mixture was washed with ether (3×9mL), and the aqueous phase was cooled with ice-water bath and acidified with conc HCl to a pH region of 1–2, and extracted with CH₂Cl₂ (3×9mL). The organic phase was dried (MgSO₄), filtered, and concentrated in vacuo to afford Cap-1 as a white solid (760mg, 87percent).

Reference： [1] Patent: WO2011/80562, 2011, A1, . Location in patent: Page/Page column 34
[2] Patent: WO2005/61487, 2005, A1, . Location in patent: Page/Page column 109
[3] Patent: US2005/159469, 2005, A1, . Location in patent: Page/Page column 56
[4] Patent: EP2423187, 2012, A1, . Location in patent: Page/Page column 11
[5] Patent: US2005/131017, 2005, A1, . Location in patent: Page/Page column 95
[6] Patent: US2005/148623, 2005, A1, . Location in patent: Page/Page column 126
[7] Organic Process Research and Development, 2004, vol. 8, # 3, p. 455 - 460
[8] Journal of Medicinal Chemistry, 1998, vol. 41, # 18, p. 3387 - 3401
[9] Organic Process Research and Development, 2008, vol. 12, # 1, p. 69 - 75
[10] Patent: US2017/28077, 2017, A1, . Location in patent: Paragraph 0136
[11] Journal of Medicinal Chemistry, 2018, vol. 61, # 9, p. 4176 - 4188
[12] Organic Process Research and Development, 2002, vol. 6, # 3, p. 323 - 328
[13] Patent: WO2008/11117, 2008, A2, . Location in patent: Page/Page column 452-453
[14] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 3, p. 255 - 258
[15] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 87 - 100
[16] Patent: WO2009/136365, 2009, A1, . Location in patent: Page/Page column 16-17
[17] Patent: US2011/178305, 2011, A1, . Location in patent: Page/Page column 6-7
[18] Patent: WO2011/107843, 2011, A2, . Location in patent: Page/Page column 15; 16
[19] Patent: US2016/297804, 2016, A1, . Location in patent: Paragraph 0154-0156

2
[ 62965-35-9 ]
[ 162537-11-3 ]

Reference： [1] Patent: EP2423187, 2012, A1,

[ 162537-11-3 ] Synthesis Path-Downstream 1~88

1
[ 870-46-2 ]
[ 162537-11-3 ]
[ 198904-77-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethyl acetate; N,N-dimethyl-formamide; at 20℃; for 18.75h;	Compound 2; EDC (l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride) (13.530 g, 77.6 mmol), HOBT (N-hydroxybenzotriazole) (10.805 g, 77.6 mmol), and 4-methylmorpholine (9.3 mL 84.7 mmol) were added to a solution ofCompound 1 (13.354 g, 70.6 mmol) in ethyl acetate (177 mL) and the resulting reaction mixture was stirred at r.t. for 45 min. Then, DMF (" dimethyl formamide") (6 mL) was added followed by tert-butyl carbazate (9.328 g, 77.6 mmol). The reaction mixture was stirred for 18 h and then was diluted with ethyl acetate. The diluted solution was washed with saturated aqueous NaHCO3 solution, water, and brine, sequentially. The combined aqueous layers were extracted with ethyl acetate and the combined organic layers were dried over Na2SO4 and concentrated to give Compound 2 as a white solid (21.417 g, 70.6 mmol, 100%). TLC R7 silica gel 60 plate, ethyl acetate/hexane, 1:1, ninhydrin stain) = 0.50.
94%		N?-(2-Methoxycarbonylamino-3, 3-dimethyl-butyryl)-hydrazinecarboxylic acid tert-butyl ester (5) (0137) Methoxycarbonyl-L-tert-Leucine (3) (1.37 gm, 7.24 mmol) was dissolved in anhydrous ethyl acetate (21 mL). To the clear solution was added N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide (EDC) (1.12 gm, 5.82 mmol, 1.1 equivalents). The suspension was stirred under nitrogen at room temperature. After ten minutes added HOBT (1.08 gm, 7.97 mmol, 1.1 equivalents), followed by 4-methyl-morpholine (1.35 mL, 12.32 mmol, 1.7 equivalents). After another 30 minutes, added t-butyl carbazate (1.05 gm, 7.97 mmol, 1.1 equivalents) and the light-yellow suspension continued stirring at room temperature. After 20 hours, the reaction mixture was diluted with ethyl acetate (50 mL) and transferred to a separatory funnel. The aqueous layer was partitioned with saturated NaHCO3. The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with saturated NaCl and dried over Na2SO4. After filtering and concentrating under reduced pressure, the residue was purified by Biotage chromatography (0 to 3% methanol/dichloromethane gradient) to give 2.05 gm (94%) of 5 as a white foam solid. 1H NMR (MeOD) delta 3.91 (bs, 1H), 3.62 (s, 3H), 1.42 (s, 9H), 0.98 (s, 9H); MS (M)+=304; HPLC tR 5.5 minutes.
90%		Example 1B; tert-butyl-2-{(2S)-2-[(methoxycarbonyl) amino] -3, 3-dimethylbutanoyl} hydrazinecarboxylate; Example 1A (8 g, 42.3 mmol) was dissolved in DMF (200 mL) and treated with EDAC (11.96 g, 1. 48 equivalent) and HOBT (8. 8 g, 1.54 equivalents) at 25C. After stirring this mixture for 15 min, t-butyl carbazate (6.1 g, 1.1 equivalent) was added, followed by N- methyl morpholine (8 mL, 1.72 equivalent) and stirring continued at 25 C for 16 h. The mixture was quenched with IN sodium bicarbonate and extracted twice with ethyl acetate. The solvents were evaporated, and the residue was purified using 30% ethyl acetate/hexanes to give 11.5 g (90%) of the title compound.

90%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25℃; for 16h;	EXAMPLE 1B Tert-butyl 2-{(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}hydrazinecarboxylate Example 1A (8 g, 42.3 mmol) was dissolved in DMF (200 mL) and treated with EDAC (11.96 g, 1.48 equivalent) and HOBT (8.8 g, 1.54 equivalents) at 25 C. After stirring this mixture for 15 min, t-butyl carbazate (6.1 g, 1.1 equivalent) was added, followed by N-methyl morpholine (8 mL, 1.72 equivalent) and stirring continued at 25 C. for 16 h. The mixture was quenched with 1N sodium bicarbonate and extracted twice with ethyl acetate. The solvents were evaporated, and the residue was purified using 30% ethyl acetate/hexanes to give 11.5 g (90%) of the title compound.
72%		Step 2: Synthesis of (S)-tert-butyl 2-(2-(methoxycarbonyla ino)-3,3- dimethylb tanoyljhydrazinecarboxylate: NH-NHBocoTo a stirred solution of <strong>[162537-11-3](S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid</strong> (step 1 , about 8.50 g, 44.97 mmol) in EtOAc ( 1 10 ml) at about 0 C l -Ethyl-3- (3-Dimethylaminopropyl)carbodiimide (9.48 g, 49.47 mmol), hydroxybenzotnazole (7.57 g, 49.47 mmol) and N-methyl morpholine (5.95 ml, 53.95 mmol) were added, after 30 minutes t-Butyl carbazate (about 6.53 g, 1 .423 mmol) was added and stirred at room temperature for about 18 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with EtOAc and washed with water, saturated NaHCCh solution and brine and the organic layer was concentrated under reduced pressure, the resulting crude was purified by silica gel column ( 100-200 mesh, elution 35% EtOAC in hexane) to afford the title compound as an off white solid. Wt: 9.8 g; Yield: 72%; NMR (300 MHz, CDC13): delta 8.83 (brs, 1 H), 6.85 (brs, 1 H), 5.71 (d, 1 H, J = 9.9 Hz), 4. 15 (d, 1 H, J = 9.6 Hz), 3.66 (s, 3H), 1 .44 (s, 9H), 1 .03 (s, 9H); Mass: [M+Na]+ 326 ( 100%); IR (KBr, cm" 1 ): 3303, 2978, 1709, 1681 , 1534, 1394, 1239. 1 162, 1060, 1020, 863, 812, 778; M.R: 65.4 C -67.6 C.

Reference： [1]Patent: WO2008/11117,2008,A2 .Location in patent: Page/Page column 453
[2]Patent: US2017/28077,2017,A1 .Location in patent: Paragraph 0137
[3]Patent: WO2005/61487,2005,A1 .Location in patent: Page/Page column 109
[4]Patent: US2005/159469,2005,A1 .Location in patent: Page/Page column 56-57
[5]Patent: WO2011/80562,2011,A1 .Location in patent: Page/Page column 34-35
[6]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401
[7]Organic Process Research and Development,2008,vol. 12,p. 69 - 75

2
[ 20859-02-3 ]
[ 79-22-1 ]
[ 162537-11-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide; In 1,4-dioxane; water; at 60℃; for 18h;pH 8 - 9;	Step 1: Synthesis of (S)-2-(methoxycarbonylaniino)-3,3-dimethylb tanoic acid:A stirred solution of (S)-2-amino-3,3-dimethylbutanoic acid (about 5.0 g, 38. 16 mmol) in Dioxane (about 20 ml) and sodium hydroxide (2N, 62 ml, PH = 8-9) at about 0 C, methychlroformate (about 5.88 ml, 76.33 mmol) was added drop wise and stirred at about 60 C for about 18 hours. The reaction mixture was cooled to room temperature, extracted with DCM, the aqueous layer was separated and acidified with I N HCl. The resulting solution was extracted with EtOAc, dried over Na2S04 and the solvent was evaporated under reduced pressure. The resulting crude was stirred in hexane and decants to afford the title compound as a solid. Wt: 8.5 g: Yield: quantitative; NMR (300 MHZ, CDCI3): delta 5.25 (d, 1 H, J = 10.5 Hz), 4. 19(d, 1 H, J = 9.6 Hz) 3.70 (s, 3H), 1 .03 (s, 9H); Mass: [M- l ]' 188 ( 100%); IR ( Br, cm 1 ): 3379, 2974, 1727, 1688, 1546, 1466, 1332, 1263. 121 1 , 1070, 1034, 1018, 843, 696.
98%	With sodium hydroxide; In 1,4-dioxane; water; at 25 - 60℃; for 22h;	Example 1; methyl (1S)-1-( (12- [ (2S, 3S)-3-amino-2-hydroxy-4-phenylbutyl]-2- [4- (2- pyridinyl) benzyl] hydrazino} carbonyl)-2, 2-dimethylpropylcarbamate; Example 1A; (2S)-2-[(methoxycarbonyl) amino] -3,3-dimethylbutanoic acid; (L)-tert-Leucine (10 g, 0.076 mol) was dissolved in 1,4-dioxane (40 mL) and treated with 2M NaOH (125 mL, 3.2 equivalents) followed by dropwise addition of methyl chlorofonnate (11.2 mL, 1.9 equivalents) at 25C. The mixture was heated at 60C for 22 hrs, cooled, and extracted twice with dichloromethane. The aqueous layer was separated, cooled in ice bath, and acidified with 4N HC1 (60 mL). The mixture was extracted three times with ethyl acetate, and the organic layer was separated, dried with sodium sulfate, filtered, and the solvents were evaporated to give 14.1 g (98%) of the title compound
98%		EXAMPLE 1A (2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoic Acid (L)-tert-Leucine (10 g, 0.076 mol) was dissolved in 1,4-dioxane (40 mL) and treated with 2M NaOH (125 mL, 3.2 equivalents) followed by dropwise addition of methyl chloroformate (11.2 mL, 1.9 equivalents) at 25 C. The mixture was heated at 60 C. for 22 hrs, cooled, and extracted twice with dichloromethane. The aqueous layer was separated, cooled in ice bath, and acidified with 4N HCl (60 mL). The mixture was extracted three times with ethyl acetate, and the organic layer was separated, dried with sodium sulfate, filtered, and the solvents were evaporated to give 14.1 g (98%) of the title compound.

98%	With sodium hydroxide; In water; at 25℃; for 2h;pH 10 - 13;Product distribution / selectivity;	Example 1 A 15% by weight sodium hydroxide aqueous solution was added to the aqueous solution (72.4 g) containing L-tert-leucine (13.2 g, 0.10 mol), to adjust the pH to 13.0. Then, methyl chloroformate (9.52 g, 0.10 mol, 1.00 equivalent) was slowly added thereto with maintaining the temperature of the mixture below 25C. At the time, the pH was decreased by adding methyl chloroformate; however, the pH of the solution was maintained at 10.0-12.8 by simultaneously adding a 15% by weight of sodium hydroxide aqueous solution. After the addition of methyl chloroformate, the mixture was stirred for 2 hours. Then, the yield and quality were analyzed by HPLC. Yield: 98%, Reaction selectivity: 100%
92%		A solution of L-tert-Leucine (25 g, 190.58 mmol) in a mixture of dioxane (100 mL) and aqueous NaOH solution (315 mL, 2N) was treated dropwise with methyl chloroformate (29.3 mL, 379.19 mmol), keeping the internal temperature below 50 C. The mixture was warmed to 60 C. and stirred for 18 hours, cooled to 25 C. and extracted with dichloromethane. The aqueous phase was cooled to 0 C. and the pH was adjusted to about 1-2 with concentrated HCl. The mixture was partitioned between ethyl acetate and water. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. A solution of the concentrate in ether was treated with hexanes to afford the crystalline product (33.22 g, 92% yield), which was collected by filtration.
92%		EXAMPLE 1F (2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoic acid A solution of L-tert-Leucine (25 g, 190.58 mmol) in a mixture of dioxane (100 mL) and aqueous NaOH solution (315 mL, 2N) was treated dropwise with methyl chloroformate (29.3 mL, 379.19 mmol), keeping the internal temperature below 50 C. The mixture was warmed to 60 C. and stirred for 18 hours, cooled to 25 C. and extracted with dichloromethane. The aqueous phase was cooled to 0 C. and the pH was adjusted to about 1-2 with concentrated HCl. The mixture was partitioned between ethyl acetate and water. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. A solution of the concentrate in ether was treated with hexanes to afford the crystalline product (33.22 g, 92% yield), which was collected by filtration.
89%	With sodium hydroxide; at 60℃; for 20h;	2-Methoxycarbonylamino-3,3-dimethyl-butyric acid (3) (0136) Into a 250 mL flask was placed L-tert-Leucine (5.0 gm, 38 mmol), 2N NaOH (66 mL), and methyl chloroformate (5.86 mL, 76 mmol, 2.0 equivalents). The reaction mixture was heated to 60 C., turning light-yellow. After approximately 20 hours, the heat was removed and the mixture cooled to room temperature, and then to 0 C. The reaction mixture was quenched at 0 C. with 2 N HCl (40 mL) to pH 1. The acidified mixture was transferred to a separatory funnel and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with water (2×150 mL), and saturated NaCl (150 mL), and then dried over Na2SO4. The organic layer was filtered and concentrated under reduced pressure to give a clear oil. The oil was azeotroped with toluene (3×50 mL), and then dried under high vacuum to give 6.4 gm (89%) of 3 as a white solid. 1H NMR (DMSO) delta 12.51 (bs, 1H), 7.28 (d, 1H), 3.80 (d, 1H), 3.53 (s, 3H), 0.93 (s, 9H); MS (M)+=190; HPLC tR 2.8 minutes.
76%		Compound 1; L-tert-leucine (12.251 g, 93.4 mmol) was dissolved in a mixture of NaOH (2N, 154 mL) and dioxane (50.5 mL). Methyl chloroformate (14.30 mL, 185.84 mmol) was added slowly (e.g., dropwise) to the solution at room temperature ("r.t."). The resulting reaction mixture was heated to 600C and stirred for 20 <n="454"/>hours ("h"). The reaction mixture was cooled to r.t. and washed with dichloromethane ("DCM.") The aqueous layer was acidified to pH 2 using concentrated HCl. The aqueous layer was then extracted with ethyl acetate, and the combined organic layers were dried over Na2SO4, and concentrated. The resulting oil was crystallized from hexane to give Compound 1 as a white solid (13.354 g, 70.6 mmol, 76%). TLC Rf (silica gel 60 plate, methanol /EXTM, 1:19) = 0.78.
71%	With sodium carbonate; sodium hydroxide; In water; at 20℃; for 3.25h;Cooling with ice;	General procedure: Na2CO3 (276mg, 2.6mmol) was added to aq NaOH (5mL of 1M/H2O, 5mmol) solution of d-valine (586mg, 5.00mmol) and the resulting solution was cooled with ice-water bath. Methyl chloroformate (0.420mL, 5.40mmol) was added dropwise, the cooling bath was removed and the reaction mixture was stirred at ambient temperature for 3.25h. The reaction mixture was washed with ether (3×9mL), and the aqueous phase was cooled with ice-water bath and acidified with conc HCl to a pH region of 1-2, and extracted with CH2Cl2 (3×9mL). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo to afford Cap-1 as a white solid (760mg, 87%).
		23.5 ml of methyl chloroformate was added over a period of 20 minutes to a solution of 20 g of 2(S)-amino-3,3-dimethyl-butyric acid in a mixture of 252 ml of 2N aqueous sodium hydroxide solution and 80 ml of dioxane and the reaction solution was heated at 600C for 14 hours. It was cooled to room temperature and then washed 2 times with methylene chloride. The aqueous phase was acidified to pH 2 with 4N aqueous hydrochloric acid and extracted three times with ethyl acetate. The organic extracts were combined, dried (Na2S O4) and concentrated by evaporation, the product started to solidify. The solidified solid was digested with hexane yielded (2S)-2-[(methoxycarbonyl)amino]- 3,3-dimethylbutanoic acid in the form of a white powder. M.p. 106-108C
		(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoic acid 23.5 ml of methyl chloroformate was added over a period of 20 minutes to a solution of 20 g of 2(S)-amino-3,3-dimethyl-butyric acid in a mixture of 252 ml of 2N aqueous sodium hydroxide solution and 80 ml of dioxane and the reaction solution was heated at 60 C. for 14 hours. It was cooled to room temperature and then washed 2 times with methylene chloride. The aqueous phase was acidified to pH 2 with 4N aqueous hydrochloric acid and extracted three times with ethyl acetate. The organic extracts were combined, dried (Na2SO4) and concentrated by evaporation, the product started to solidify. The solidified solid was digested with hexane yielded (2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoic acid in the form of a white powder. M.p. 106-108 C.
		L-tert-leucine (100 g, 0.76 mole, D-isomer = 0.35%) was added to a mixture of sodium hydroxide (100 g) in 1250 ml_ water and methyl chloroformate (144.3 g, 1.5 mole). Heated at 60C for 18 hours. Cooled to 25C, acidified with concentrated HCI and extracted with ethyl acetate. Organic layer was concentrated under reduced pressure to obtain viscous oil. Pure N-methoxy carbonyl-(L)-tert-leucine (0.2 g) and n-heptane added, stirred for 1 hour and solid was filtered.The wet solid (-130 g) was stirred in mixture ethyl acetate (120 mL), and n-heptane (700 mL) at 50 - 85C to get clear solution. Cooled to 25 - 30C. Pure N-methoxycarbonyl-(L)- tert-leucine (0.2 g) was added, stirred for 1 hour, solid was filtered, washed with n-heptane and dried under reduced pressure to give 1 10 g of N-methoxycarbonyl-(L)-tert-leucine (D- isomer was below detection limit by HPLC).
	With sodium carbonate; sodium hydroxide; In water; at 0 - 20℃; for 4.33h;	2 g (S)-2-amino-3,3-dimethyl butyric acid was weighted into a 100 mL eggplant-shaped flask, 15.27 mL aqueous NaOH solution (1 M) and 809 mg sodium carbonate were added thereto, and at 0-4 C., 1.3 mL methyl chloroformate was added dropwise slowly. After the addition, the reaction was continued at 0-4 C. for 20 min, then at room temperature for 4 h, and then cooled to 0 C. After diluting the reaction mixture by adding 20 mL diethyl ether, 3 mL concentrated hydrochloric acid was slowly added dropwise. The mixture was extracted with ethyl acetate (250 mL). The combined organic phase was washed with saturated brine (150 mL), dried over anhydrous sodium sulfate, filtered, concentrated and purified by column chromatography to give the title compound. LC-MS m/z: [M+H]=190.

Reference： [1]Patent: WO2011/80562,2011,A1 .Location in patent: Page/Page column 34
[2]Patent: WO2005/61487,2005,A1 .Location in patent: Page/Page column 109
[3]Patent: US2005/159469,2005,A1 .Location in patent: Page/Page column 56
[4]Patent: EP2423187,2012,A1 .Location in patent: Page/Page column 11
[5]Patent: US2005/131017,2005,A1 .Location in patent: Page/Page column 95
[6]Patent: US2005/148623,2005,A1 .Location in patent: Page/Page column 126
[7]Organic Process Research and Development,2004,vol. 8,p. 455 - 460
[8]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401
[9]Organic Process Research and Development,2008,vol. 12,p. 69 - 75
[10]Patent: US2017/28077,2017,A1 .Location in patent: Paragraph 0136
[11]Journal of Medicinal Chemistry,2018,vol. 61,p. 4176 - 4188
[12]Organic Process Research and Development,2002,vol. 6,p. 323 - 328
[13]Patent: WO2008/11117,2008,A2 .Location in patent: Page/Page column 452-453
[14]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 255 - 258
[15]European Journal of Medicinal Chemistry,2017,vol. 125,p. 87 - 100
[16]Patent: WO2009/136365,2009,A1 .Location in patent: Page/Page column 16-17
[17]Patent: US2011/178305,2011,A1 .Location in patent: Page/Page column 6-7
[18]Patent: WO2011/107843,2011,A2 .Location in patent: Page/Page column 15; 16
[19]Patent: US2016/297804,2016,A1 .Location in patent: Paragraph 0154-0156
[20]European Journal of Medicinal Chemistry,2019,vol. 167,p. 245 - 268

3
[ 162537-11-3 ]
[ 198904-57-3 ]
CGP 75136 [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

4
[ 162537-11-3 ]
[ 191594-67-9 ]
[ 191594-71-5 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

5
[ 162537-11-3 ]
[ 198905-12-3 ]
[ 198905-04-3 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

6
[ 162537-11-3 ]
[ 198904-46-0 ]
[ 198904-47-1 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

7
[ 162537-11-3 ]
(2S,3S)-3-Amino-1-(N-biphenyl-4-ylmethyl-hydrazino)-4-phenyl-butan-2-ol; hydrochloride [ No CAS ]
CGP 75355 [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

8
[ 162537-11-3 ]
[ 198904-48-2 ]
1-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis-[N-(N-methoxycarbonyl-(L)-tert-leucyl)-amino]-6-phenyl-2-azahexane [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

9
[ 162537-11-3 ]
[ 198904-61-9 ]
{(S)-1-[N'-[(2S,3S)-2-Hydroxy-3-((S)-2-methoxycarbonylamino-3-methyl-butyrylamino)-4-phenyl-butyl]-N'-(4-thiazol-2-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

10
[ 162537-11-3 ]
[ 198904-50-6 ]
{(S)-1-[N'-[(2S,3S)-2-Hydroxy-3-((S)-2-methoxycarbonylamino-3-methyl-butyrylamino)-4-phenyl-butyl]-N'-(4-thiazol-5-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

11
[ 162537-11-3 ]
1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride [ No CAS ]
[ 198904-31-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With 4-methyl-morpholine; diisopropyl-carbodiimide; In dichloromethane; isopropyl alcohol; at -10 - 20℃;Inert atmosphere;Product distribution / selectivity;	Example 1 : Preparation of atazanavir using 1 equivalent of compound (II), 3.5 equivalents of compound (III), 3.5 equivalents of DIC, and 6.6 equivalents of NMM97.5 g of 1 -[4-(piridyn-2-yl)phenyl-4(S)-hydroxy]-5-(S)-2,5-diamino-6-phenyl- 2-azahexane trihydrochloride (trihydrochloride of compound (II) with a 10%wt content of isopropanol, 185.97mmol) were suspended into 683 ml of dichloromethane under nitrogen atmosphere at -10 0C. 135 ml_ (1227.40 mmol) of /V-methylmorpholine were added maintaining the temperature at -10 0C.Separately, 100.8 ml_ (650.90 mmol) of N,N-diisopropylcarbodiimide were added to a suspension of 123.2 g (650.90 mmol) of N-(methoxycarbonyl)-L- tert-leucine (compound (III)) into 975 ml of dichloromethane.Then, the first suspension was quickly transferred over the second one. The resulting mixture was warmed up to room temperature and was maintained at such temperature until the reaction was completed (93% atazanavir by HPLC, monoimpurity content: 1.2%). The reaction mixture was filtered off and was washed with 800 ml_ of water. Then, the organic phase was concentrated up to half volume and 500 ml_ of tert-butylmethylether were added. The mixture was concentrated again up to half volume. This operation was repeated three times up to a dichloromethane content equal or less to 20%. The precipitated product was recovered by filtration. 125.4 g of atazanavir were obtained (Yield =96%). Purity by High Performance Liquid Chromatography (HPLC) = 98.2%, with 4% of N,N-diisopropylurea (DIU) and free of the other probable diastereomers. Molar yield =92%. Recrystallization in ethanol/water 45:55 yielded 105.34 g of atazanavir (149.5 mmol). Recrystallization yield: 84%. Purity HPLC = 99.4%, free of DIU, and free of the other probable diastereomers.The formula of the three probable diastereomers and the HPLC conditions to detect their presence are included below:d-ld-ll d-lHPLC conditions:Liquid chromatograph with UV detector equipped with automatic injector, and integration systemColumn: ZORBAX Eclipse XDB-C18 150x4.6 mm, 5mum.Mobile phase: A (0.05% formic acid in water) and B (ACN)Gradient elution:Detection: 254 nmFlow: 1 mL/minColumn temperature: 25 0CInjection: 2 muLTime injection and chromatogram: 20 minRelative retention time of the diastereomers (RRT):

Reference： [1]Patent: WO2010/146119,2010,A1 .Location in patent: Page/Page column 9-11
[2]Organic Process Research and Development,2002,vol. 6,p. 323 - 328
[3]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

12
[ 162537-11-3 ]
(2S,3S)-3-Amino-1-[N-(4-diethylamino-benzyl)-hydrazino]-4-phenyl-butan-2-ol; hydrochloride [ No CAS ]
[ 202586-00-3 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

13
[ 162537-11-3 ]
(2S,3S)-3-Amino-1-{N-[4-(2-methyl-2H-tetrazol-5-yl)-benzyl]-hydrazino}-4-phenyl-butan-2-ol; hydrochloride [ No CAS ]
CGP 75176 [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

14
[ 162537-11-3 ]
{(S)-1-[(1S,2S)-1-Benzyl-3-(N-biphenyl-4-ylmethyl-hydrazino)-2-hydroxy-propylcarbamoyl]-2-methyl-propyl}-carbamic acid methyl ester; hydrochloride [ No CAS ]
((S)-1-{N'-Biphenyl-4-ylmethyl-N'-[(2S,3S)-2-hydroxy-3-((S)-2-methoxycarbonylamino-3-methyl-butyrylamino)-4-phenyl-butyl]-hydrazinocarbonyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

15
[ 162537-11-3 ]
{(S)-1-[(1S,2S)-1-Benzyl-3-(N-biphenyl-4-ylmethyl-hydrazino)-2-hydroxy-propylcarbamoyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester; hydrochloride [ No CAS ]
((S)-1-{(1S,2S)-1-Benzyl-3-[N-biphenyl-4-ylmethyl-N'-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-hydrazino]-2-hydroxy-propylcarbamoyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

16
[ 162537-11-3 ]
((S)-1-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N-(4-pyridin-2-yl-benzyl)-hydrazino]-propylcarbamoyl}-2-methyl-propyl)-carbamic acid methyl ester; hydrochloride [ No CAS ]
{(S)-1-[N'-[(2S,3S)-2-Hydroxy-3-((S)-2-methoxycarbonylamino-3-methyl-butyrylamino)-4-phenyl-butyl]-N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

17
[ 162537-11-3 ]
1-[4-(2-tert-butyl-2H-tetrazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-amino-2-N-[N-methoxycarbonyl-(L)-tert-leucyl]amino-6-phenyl-2-azahexane hydrochloride [ No CAS ]
((S)-1-{N'-[4-(2-tert-Butyl-2H-tetrazol-5-yl)-benzyl]-N'-[(2S,3S)-2-hydroxy-3-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyrylamino)-4-phenyl-butyl]-hydrazinocarbonyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

18
[ 162537-11-3 ]
C₁₆⁽¹³⁾C₆H₂₆N₄O*3ClH [ No CAS ]
[ring-13C₆]-1-[4-(pyridin-2-yl)phenyl]-5(S)-2,5-bis[N-(methoxy-carbonyl)-L-tert-leycinyl]amino}-4(S)-hydroxy-6-phenyl-2-azahexane [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 123 - 130

19
[ 252870-78-3 ]
[ 162537-11-3 ]
((S)-1-{(1S,2R)-1-Benzyl-3-[cyclopentyloxy-(4-methoxy-benzenesulfonyl)-amino]-2-hydroxy-propylcarbamoyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3560 - 3564

20
[ 20570-96-1 ]
[ 162537-11-3 ]
[ 872703-56-5 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 8098 - 8102

21
[ 45811-94-7 ]
[ 162537-11-3 ]
[ 872703-59-8 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 8098 - 8102
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

22
[ 920757-34-2 ]
[ 162537-11-3 ]
{2,2-dimethyl-1-[<i>N</i>-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester [ No CAS ]
[ 857904-02-0 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 1041 - 1047

23
[ 857900-54-0 ]
[ 162537-11-3 ]
[ 198904-31-3 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 1041 - 1047

24
3-bromobenzylhydrazine [ No CAS ]
[ 162537-11-3 ]
[ 882435-39-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethyl acetate; at 20℃;	N-(Methoxycarbonyl)-(L)-tert-leucine (3.25 g, 17.1 mmol) was dissolved in EtOAc(40 mL) and HOBT (2.55 g, 18.9 mmol), EDAC (3.62 g, 18.9 mmol) and NuMM (2.08 mL, 18.9 mmol) were added subsequently. 3-Bromo-benzylhydrazine (4.14 g, 20.6 mmol), dissolved in EtOAc (20 mL) was added to the reaction mixture, which thereafter was stirred at room temperature over night. The organic phase was washed with saturated NaHCO3 (aq., 50 mL), H2O (50 mL) and brine (50 mL). The combined aqueous phases were extracted with EtOAc (3x50 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (silica, CHCl3MeOH, 100:0-95:5) to afford 2 (4.88 g, 76%). RP-LC-MS (35 min gradient of 35-80% CH3CN in 0.05% aqueous formic acid) was performed on a small fraction of the residue to obtain a sample of higher purity for characterization and the product was isolated as a white solid. [alpha]D20 -28.0 (c 1.2, CH3OH);1H NMR (CD3OD) delta 7.56 (m, IH), 7.40 (m, IH), 7.32 (m, IH), 7.22 (m, IH), 3.93 (s, 2H), 3.81 (s, IH), 3.63 (s, 3H), 0.89 (s, 9H); 13C NMR (CD3OD) delta 171.7, 159.0, 141.8, 132.9, 131.5, 131.1, 128.8, 123.3, 62.9, 55.5, 52.7, 35.1, 26.9; MS (m/z 372, M + H+, 374, M + H+).

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832
[2]Patent: WO2006/84688,2006,A1 .Location in patent: Page/Page column 78

25
C₃₂H₄₂N₄O₆S [ No CAS ]
[ 162537-11-3 ]
C₄₀H₅₅N₅O₉S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 1.75h;	Example R; A solution of EDC (27.4 mg, 0.14 mmol), HOBT (19.3 mg, 0.14 mmol), and Compound 1 (27.1 mg, 0.14 mmol) in DMF (2.0 mL) was stirred for 45 minutes before 4-methylmorpholine (41 muL, 0.37 mmol) and Compound 26 (67.2 mg, 0.11 mmol) were added. The reaction mixture was stirred at r.t. for 1 h before the reaction was concentrated. The residue was purified by reverse phase HPLC (Phenomenex Synergi column, 25-100% acetonitrile/H-O) and yielded Example R as a white solid (22.4 mg, 0.02 mmol, 26%). 1H NMR (300 MHz,CD3OD): delta 7.81 (d, J = 8.4, 2 H), 7.45 (d, J = 8.1, 2 H), 7.09 (m, 3 H), 6.75 (d, J = 8.4, 2 H), 5.53 (d, J = 5.4, 1 H), 4.87 (m, 1 H), 3.55-3.94 (m, 15 H), 2.70-2.85 (m, 5 H), 1.05-1.60 (m, 11 H), 0.70 (s, 9 H). Mass spectrum: (M+H)+ = 782.2, (M+Na)+ = 804.3.

Reference： [1]Patent: WO2008/11117,2008,A2 .Location in patent: Page/Page column 476

26
C₂₇H₃₇N₄O₅P [ No CAS ]
[ 162537-11-3 ]
C₄₃H₆₃N₆O₁₁P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 1.33333h;	Example AB; TPTU (1.01 g, 3.4 mmol, 3.0 eq.) was added to Compound 1 (prepared following the procedure of Journal of Medicinal Chemistry, 1998, 41, 3399) (644 mg, 3.0 eq.) in 6 mL DCM at room temperature and stirred for 5 minutes. DIEA (1.19 mL, 3.0 eq.) was added to the mixture at 00C. The mixture was stirred at 00C for 30 minutes. The reaction mixture was added to a solution of Compound 40 (600 mg, 1.135 mmol, 1.0 eq.) in 5 mL of DCM at 00C. The reaction mixture was stirred at 00C, and warmed to room temperature overnight. The reaction mixture was then extracted using DCM (3X) /saturated NaHCO3 solution. The organic layer was dried (Na2SO4) and concentrated. The residue was purified using silica gel chromatography (4-8% MeOH/DCM) to give white solid (557 mg, 56%). LC-MS shows 871.1 (M+H)+. 1H NMR (300 MHz, CDCl3): delta 8.78(d, 1 H), 7.94 (d, 2 H), 7.78(m, 2 H), 7.42 (d, 2 H), 7.22 (m, 1 H), 7.18 (d, 2 H), 6.80 (d, 2 H), 6.50 (d, 1 H), 5.52 (d, 1 H), 5.38 (d, 1 H), 4.20 (m, 6 H), 4.00 (m, 2 H), 3.80 (m, 1 H), 3.60 (m, 7 H), 2.84 (m, 3 H), 2.56 (m, 1 H), 1.35 (dd, 6 H)70.82 (s, 9 H), 0.78 (s, 9 H). 31P NMR (300 MHz7 CDCl3): 519.543.

Reference： [1]Patent: WO2008/11117,2008,A2 .Location in patent: Page/Page column 489

27
[ 162537-11-3 ]
[ 144164-11-4 ]
N₁-((1S,3S,4S)-1-benzyl-3-hydroxy-5-phenyl-4-[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}pentyl)-N₂-(methoxycarbonyl)-3-methyl-L-valinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.5%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 16h;	[00267] Example 7. Preparation of N'-((lS,3S,4S)-l-benzyl-3-hydroxy-5-phenyl-4-[(1,3-thiazol-5- ylmethoxy)carbonyl]amino}pentyl)-N2-(methoxycarbonyl)-3-methyl-L-valinamide; [00268] A solution of 1 ,3-thiazol-5-ylmethyl ( 1 S,2S,4S)-4-amino- 1 -benzyl-2-hydroxy-5-phenylpentyl carbamate (50 mg, 0.1 mmol), l-(3-dimethylaminopropyI)-3-ethylcarbodiimide hydrochloride (29.7 mg, 1.5 equivalents), and 1-hydroxybenzotriazole (20.4 mg, 1.5 equivalents) in N,N-dimethylformamide (0.5 mL) was stirred for 5 minutes at room temperature. To this mixture was added L-tert-leucine methyl carbamate (21 mg, 1.1 equivalents) followed by N-methylmorpholine (50 muL, 4.5 equivalents) and the solution was stirred for 16 hours. The reaction mixture was quenched with saturated sodium bicarbonate, extracted with EtOAc, washed with 10% citric acid, dried (Na2SO4), and concentrated in vacuo. Column chromatography on silica (8% MeOH/ CH2Cl2) gave a white foam (44 mg, 73.5%). IH NMR (300 MHz, DMSO-D6) delta ppm 0.81 (s, 9 H), 1.39 - 1.52 (m, 2 H), 2.55 - 2.71 (m, 4 H), 3.48 - 3.66 (m, 4 H), 3.82 (d, <n="99"/>J=9.56 Hz, 2 H), 4.05 - 4.23 (m, 1 H), 4.64 (d, J=6.25 Hz, 1 H), 5.04 - 5.30 (m, 2 H), 6.69 (d, ^=9.56 Hz, 1 H), 6.90 (d, J=9.56 Hz, 1 H), 7.05 - 7.29 (m, 10 H), 7.71 - 7.82 (m, 1 H), 7.86 (s, 1 H), 9.05 (s, 1 H); MS(ESI) m/z 597.3 (M+H)+.

Reference： [1]Patent: WO2008/27932,2008,A2 .Location in patent: Page/Page column 97-98

28
[ 162537-11-3 ]
[ 156732-15-9 ]
C₄₀H₄₉N₃O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4316 - 4328

29
[ 952196-23-5 ]
[ 162537-11-3 ]
C₂₇H₄₆N₄O₆ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4316 - 4328

30
C₂₄H₃₂N₄O₄ [ No CAS ]
[ 162537-11-3 ]
C₃₂H₄₅N₅O₇ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4316 - 4328

31
[ 162537-11-3 ]
[ 854754-08-8 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4316 - 4328

32
[ 162537-11-3 ]
C₃₆H₄₄N₄O₇ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4316 - 4328

33
[ 162537-11-3 ]
[ 872703-69-0 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 8098 - 8102

34
[ 162537-11-3 ]
[ 882435-40-7 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

35
[ 162537-11-3 ]
{(S)-1-[N'-[(S)-2-Hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-(3-pyridin-4-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

36
[ 162537-11-3 ]
{(1S)-1-[N'-(biphenyl-3-yl-methyl)-N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

37
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-[3-(pyridin-3-yl)-benzyl]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

38
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-[4-(pyridin-3-yl)-benzyl]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

39
[ 162537-11-3 ]
{(1S)-1-[N'-(biphenyl-4-yl-methyl)-N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

40
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-[4-(pyridin-2-yl)-benzyl]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

41
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-[4-(pyridin-4-yl)-benzyl]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

42
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-[3-(pyridin-2-yl)-benzyl]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

43
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-[4-(pyrazin-2-yl)-benzyl]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

44
[ 162537-11-3 ]
((1S)-1-{N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-[4-((E)-styryl)-benzyl]-hydrazinocarbonyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

45
[ 162537-11-3 ]
((1S)-1-{N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-[3-((E)-styryl)-benzyl]-hydrazinocarbonyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

46
[ 162537-11-3 ]
{(S)-1-[N'-[(S)-2-Hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-(3-pyridin-3-ylethynyl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

47
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-(4-pyridin-2-ylethynyl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

48
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N-(4-phenylethynyl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

49
[ 162537-11-3 ]
{(1S)-1-[N'-[4-(3,5-dimethyl-isoxazol-4-yl)-benzyl]-N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

50
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-(4-pyridin-3-ylethynyl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

51
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-[3-(pyridin-2-ylethynyl)-benzyl]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

52
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-(3-phenylethynyl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

53
[ 162537-11-3 ]
{(1S)-1-[N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-N'-[4-(benzo[b]thiophen-2-yl)-benzy]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

54
[ 162537-11-3 ]
{(1S)-1-[N'-(4-benzo[1,3]dioxol-5-yl-benzyl)-N'-[(2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl]-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1828 - 1832

55
[ 162537-11-3 ]
[ 857900-54-0 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 1041 - 1047
[2]Patent: WO2011/80562,2011,A1
[3]Patent: US2017/28077,2017,A1

56
[ 162537-11-3 ]
[ 857904-03-1 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 1041 - 1047
[2]Patent: WO2011/80562,2011,A1

57
[ 162537-11-3 ]
{(1S)-1-[N'-benzyl-N'-((2S)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 8098 - 8102

58
[ 162537-11-3 ]
{(1S)-1-[N'-benzyl-N'-((2R)-2-hydroxy-2-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 8098 - 8102

59
[ 162537-11-3 ]
C₃₈H₄₉⁽²⁾H₃N₆O₇ [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 1041 - 1047

60
[ 162537-11-3 ]
[ 198904-31-3 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 1041 - 1047
[2]Organic Process Research and Development,2008,vol. 12,p. 69 - 75
[3]Organic Process Research and Development,2008,vol. 12,p. 69 - 75
[4]Patent: US2018/71270,2018,A1

61
[ 162537-11-3 ]
[ 198904-78-8 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401
[2]Patent: WO2011/80562,2011,A1

62
[ 162537-11-3 ]
{(S)-2,2-Dimethyl-1-[1-[4-(2H-tetrazol-5-yl)-phenyl]-meth-(E)-ylidene-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

63
[ 162537-11-3 ]
{(S)-1-[1-[4-(2-tert-Butyl-2H-tetrazol-5-yl)-phenyl]-meth-(E)-ylidene-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

64
[ 162537-11-3 ]
[ 198904-81-3 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

65
[ 162537-11-3 ]
[ 198904-48-2 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

66
[ 162537-11-3 ]
{(S)-1-Benzyl-3-[N-[4-(2-tert-butyl-2H-tetrazol-5-yl)-benzyl]-N'-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyryl)-hydrazino]-2-oxo-propyl}-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

67
[ 162537-11-3 ]
((S)-1-{(1S,2S)-1-Benzyl-3-[N-biphenyl-4-ylmethyl-N'-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-hydrazino]-2-hydroxy-propylcarbamoyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

68
[ 162537-11-3 ]
((S)-1-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N'-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-N-(4-pyridin-2-yl-benzyl)-hydrazino]-propylcarbamoyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

69
[ 162537-11-3 ]
((S)-1-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N'-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-N-(4-thiazol-5-yl-benzyl)-hydrazino]-propylcarbamoyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

70
[ 162537-11-3 ]
1-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis-[N-(N-methoxycarbonyl-(L)-tert-leucyl)-amino]-6-phenyl-2-azahexane [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

71
[ 162537-11-3 ]
((S)-1-{(1S,2S)-1-Benzyl-3-[N'-((S)-2-ethoxycarbonylamino-3-methyl-butyryl)-N-(4-thiazol-5-yl-benzyl)-hydrazino]-2-hydroxy-propylcarbamoyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

72
[ 162537-11-3 ]
{(S)-1-[(1S,2S)-1-Benzyl-3-(N-biphenyl-4-ylmethyl-hydrazino)-2-hydroxy-propylcarbamoyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester; hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

73
[ 162537-11-3 ]
1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane dihydrochioride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

74
[ 162537-11-3 ]
((S)-1-{N'-[4-(2-tert-Butyl-2H-tetrazol-5-yl)-benzyl]-N'-[(2S,3S)-2-hydroxy-3-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyrylamino)-4-phenyl-butyl]-hydrazinocarbonyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

75
[ 162537-11-3 ]
1-[4-(2-tert-butyl-2H-tetrazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-amino-2-N-[N-methoxycarbonyl-(L)-tert-leucyl]amino-6-phenyl-2-azahexane hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3387 - 3401

76
[ 630423-83-5 ]
[ 162537-11-3 ]
[ 630423-84-6 ]

Yield	Reaction Conditions	Operation in experiment
54%	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃;	To a solution of above compound (200 mg, 0.527 mmol) in CH3CN (10 mL) was added 2-methoxycarbonylamino-3, 3-dimethyl-butyric acid (0.15 g, 0.79 mmol), DIEA (0.46 mL, 2.63 mmol) and the coupling reagent HOBt (0.121 g, 0.79 mmol) and HBTU (0.30 g, 0.79 mmol). The solution was stirred at rt. overnight. Then it was concentrated, washed with water and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over MgS04 and concentrated to give yellowish oil. It was purified by Prep. HPLC column to give white solid as final product (intermediate 2). (145 mg, 54% yield) 'H NMR (CD30D, 500 MHz)8 0.99-1. 10 (m, 11 H), 1.24 (m, 2 H), 1.41 (dd, J=9. 5, 5.5 Hz, 1 H), 1.87 (dd, J=7. 9,5. 5 Hz, 1 H), 1.97 (m, 1 H), 2.13 (m,1 H), 2.24 (m,1 H), 2.93 (m,1 H), 3.65 (s, 3 H), 3.77-3. 88 (m, 2 H), 4.33-4. 39 (m, 2 H), 4.49 (m, br, 1 H), 5.13 (d, J=10. 4 Hz,1 H), 5.31 (d,J=17. 1 Hz,1 H), 5.76 (m, 1 H). LC-MS (retention time: 1.590 min. ), MS m/z 515(MH+).

Reference： [1]Patent: WO2003/99274,2003,A1 .Location in patent: Page 441-442

77
4-[2-(3,4-dihydro-1H-isoquinolin-2-yl)-pyrimidin-4-yloxy]-pyrrolidine-2-carboxylic acid (1-cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-amide hydrochloride [ No CAS ]
[ 162537-11-3 ]
C₃₅H₄₅N₇O₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃;	To a solutionof 4- [2- (3, 4-Dihydro-lH-isoquinolin-2-yl)-pyrimidin-4-yloxy]- pyrrolidine-2-carboxylic acid (1-cyclopropanesulfonylaminocarbonyl-2-vinyl- cyclopropyl)-amide hydrochloride (20 mg, 0.032 mmol) in CH3CN (5 mL) was added 2-methoxycarbonylamino-3, 3-dimethyl-butyric acid (9.1 mg, 0.048 mmol), DIEA (0.028 mL, 0.16 mmol) and the coupling reagent HOBt (7.3 mg, 0.048 mmol) and HBTU (18.2 mg, 0.048 mmol). The solution was stirred at rt. overnight. Then it was concentrated, washed with water and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over MgS04 and concentrated to give yellowish oil. It was purified by Prep. HPLC column to give a colorless oil as TFA salt (Compound 341). (16 mg, 60% yield) 'H NMR (CD30D, 500 MHz) 0.98-1. 06 (m, 13 H), 1.13 (m, 1 H), 1.22-1. 32 (m,1 H), 1.35-1. 44 (m, 1 H), 1.82 (dd, J=8. 24,5. 19 Hz, 0.5 H), 1.90 (dd, J=8. 24,5. 49 Hz, 0.5 H), 2.26 (m,1 H), 2.32-2. 43 (m,1 H), 2.56 (m,1 H), 2.96 (m, 1 H), 3.11 (m, br, 2 H), 3.56 (s, 3 H), 4.14 (m,1 H), 4.21 (m, 1 H), 4.38 (m,1 H), 4.47 (m, 1 H), 5.15 (m, 1 H), 5.31 (m,1 H), 5.75 (m,1 H), 5.94 (s,1 H), 6.47 (d,J=7. 02 Hz, 1 H), 7.29 (s, 4 H), 7.49 (m, 1 H), 7.56 (m, 1 H), 7.74 (d, J=8. 24 Hz,1 H), 7.88 (d, J=8. 24 Hz,1 H), 8.11 (d, J=7.02 Hz, 1 H). LC-MS (retention time: 1.517 min. ), MS m/z 724(MH+).

Reference： [1]Patent: WO2003/99274,2003,A1 .Location in patent: Page 455-456

78
4-(quinolin-4-yloxymethyl)-pyrrolidine-2-carboxylic acid methyl ester bis hydrochloride [ No CAS ]
[ 162537-11-3 ]
[ 630423-95-9 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃;	To a solution of4- (quinolin-4-yloxymethyl)-pyrrolidine-2-carboxylic acid methyl ester bis hydrochloride salt (110 mg, 0.306 mmol) in CH3CN (10 mL) was added 2- methoxycarbonylamino-3,3-dimethyl-butyric acid (87 mg, 0.46 mmol), DIEA (0.27 mL, 1.53 mmol) and the coupling reagent HOBt (70 mg, 0.46 mmol) and HBTU (174 mg, 0.46 mmol). The solution was stirred at rt. overnight. Then it was concentrated, washed with water and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over MgS04 and concentrated to give yellowish oil. It was purified by Prep. HPLC column to give colorless oil as TFA salt. (105 mg, 60% yield)'H NMR(CD30D, 500 MHz)S 1.07 (s, 9 H). 2.34 (m, 1 H), 2.45 (m,1 H), 3.14 (m,1 H), 3.27 (s, 3 H), 3.75 (s, 3 H), 4.05 (m, 1 H), 4.20 (m, 1 H), 4.31 (s,1 H), 4.57- 4.63 (m, 2 H), 4.73 (m,1 H), 7.53 (d, J=6. 7 Hz, 1 H), 7.91 (t, J=7. 6 Hz,1 H), 8.06- 8.16(m, 2 H), 8.43 (d, J=8. 6 Hz, 1 H), 9.02 (d, J=6. 4 Hz,1 H). LC-MS (retention time: 1.250 min. ), MS m/z 458(MH+).

Reference： [1]Patent: WO2003/99274,2003,A1 .Location in patent: Page 461-462

79
[ 630424-01-0 ]
[ 162537-11-3 ]
[ 630424-03-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃;	To a solution of4- (5-Bromo-pyridin-3-yloxymethyl)-pyrrolidine-2-carboxylic acid methyl ester (70 mg, 0.129 mmol) in CH3CN (10 mL) was added 2methoxycarbonylamino-3, 3-dimethyl-butyric acid (36.5 mg, 0.193 mmol), DIEA (0.135 mL, 0.744 mmol) and the coupling reagent HOBt (30 mg, 0.193 mmol) and HBTU (73 mg, 0.193 mmol). The solution was stirred at rt. overnight. Then it was concentrated, washed with water and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over MgS04 and concentrated. It was then purified by Prep. HPLC column to give colorless oil as product. (80 mg, 100% yield)'H NMR(CD30D, 400 MHz)6 1.04 (s, 9 H), 2.17 (m,1 H), 2.26 (m, 1 H), 2.87 (m,1 H), 3.50 (s, 3 H), 3.70 (s, 3 H), 3.88-3. 98 (m, 2 H), 4.04-4. 12 (m, 2 H), 4.28 (s,1 H), 4.60 (dd, J=9. 05,5. 87 Hz,1 H), 7.86 (m,1 H) 8.31-8. 35 (m, 2 H). LC-MS (retention time: 1.697min.), MS m/z 486(MH+).

Reference： [1]Patent: WO2003/99274,2003,A1 .Location in patent: Page 467-468

80
[ 767285-53-0 ]
[ 162537-11-3 ]
[ 630424-06-5 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃;	To a solution of crude4- (2-Bromo-pyridin-4-yloxymethyl)-pyrrolidine-2-carboxylic acid methyl ester inCH3CN (20 mL) was added 2-methoxycarbonylamino-3,3- dimethyl-butyric acid (312 mg, 1.65 mmol), DIEA (1.15 mL, 6.6 mmol) and the coupling reagent HOBt (252 mg, 1.65 mmol) and HBTU (626 mg, 1.65 mmol). The solution was stirred at rt. overnight. Then it was concentrated, washed with water and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over MgS04 and concentrated. It was then purified by Prep. HPLC column to give colorless oil as product. (270 mg, 41% yield two steps) 'H NMR(CD30D, 400 MHz) 1.03 (s, 9 H), 2.13-2. 19 (m, 2 H), 2.87(m, 1 H), 3.51 (s, 3 H), 3.70 (s, 3 H), 3.93 (d, J=6. 36 Hz, 2 H), 4.11(m, 2 H), 4.27 (s,1 H), 4.60 (dd, J=8. 80,5. 87 Hz,1 H), 7.06 (d, J=5. 87,2. 20 Hz,1 H) 7.32 (d, J=2. 20 Hz, 1 H), 8.18 (d, J=6.11 Hz, 1 H). LC-MS (retention time: 1.657 min. ), MS m/z 486(MH+).

Reference： [1]Patent: WO2003/99274,2003,A1 .Location in patent: Page 473

81
[ 854816-62-9 ]
[ 162537-11-3 ]
methyl (1S)-1-[({(1S,2S,4S)-4-[((2S)-3,3-dimethyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2-oxo-1-imidazolidinyl}butanoyl)amino]-2-hydroxy-1-[4-(4-methyl-2-pyridinyl)benzyl]-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; at 25℃; for 16h;	A solution containing the product from Example 80E (0.068 mmol) in THF (0.65 mL) was treated with the product from Example 1F (0.017 g, 0.088 mmol), DEPBT (0.030 g, 0.102 mmol), and N,N-diisopropylethylamine (0.118 mL, 0.678 mmol), stirred at 25 C for 16 hours, and partitioned between ethyl acetate and 10% Na2CO3 solution. The organic phase was washed with additional 10% Na2CO3 solution and brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with 0-100% ethyl acetate/dichloromethane, followed by 0-5% methanol in ethyl acetate, to give the title compound (0.036 g, 64% yield). 1H NMR (300 MHz, DMSO-d6), delta ppm 0.83 (s, 9H), 0.86 (s, 9H), 1.53 (m, 2H), 2.42 (m, 8H), 2.73 (m, 3H), 3.03 (m, 2H), 3.23 (m, 1H), 3.52 (s, 3H), 3.62 (m, 1H), 3.94 (m, 2H), 4.18 (m, 2H), 4.34 (m, 2H), 4.83 (d, J=5.88 Hz, 1H), 6.79 (d, J=9.56 Hz, 1H), 7.05 (m, 6H), 7.16 (m, 2H), 7.29 (d, J=8.09 Hz, 2H), 7.58 (d, J=8.46 Hz, 1H), 7.69 (m, 2H), 7.90 (d, J=8.46 Hz, 3H), 8.48 (d, J=4.78 Hz, 1H).

Reference： [1]Patent: US2005/131017,2005,A1 .Location in patent: Page/Page column 133

82
tert-butyl (1S,2S,4R)-4-amino-1-benzyl-2-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate hydrochloride salt [ No CAS ]
[ 162537-11-3 ]
methyl (S)-1-((2R,4S,5S)-5-(tert-butoxycarbonyl)amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; at 25℃; for 16h;	A solution of the product of Example 1E (1.7 g) in THF (33 mL) was treated with the product of Example 1F (0.81 g, 4.3 mmol), DEPBT (1.5 g, 5.0 mmol), and N,N-diisopropylethylamine (2.9 mL, 16.6 mmol), stirred at 25 C. for 16 hours, and partitioned between ethyl acetate and 10% Na2CO3 solution. The organic phase was washed with additional 10% Na2CO3 solution and brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-100% ethyl acetate/dichloromethane to give the title compound (1.55 g, 74% yield).
74%	With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; at 25℃; for 16h;	EXAMPLE 1G tert-butyl(1S,2S,4R)-1-benzyl-2-hydroxy-4-({(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}amino)-5-[4-(2-pyridinyl)phenyl]pentylcarbamate A solution of the product of Example 1E (1.7 g) in THF (33 mL) was treated with the product of Example 1F (0.81 g, 4.3 mmol), DEPBT (1.5 g, 5.0 mmol), and N,N-diisopropylethylamine (2.9 mL, 16.6 mmol), stirred at 25 C. for 16 hours, and partitioned between ethyl acetate and 10% Na2CO3 solution. The organic phase was washed with additional 10% Na2CO3 solution and brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluding with 0-100% ethyl acetate/dichloromethane to give the title compound (1.55 g, 74% yield).

Reference： [1]Patent: US2005/131017,2005,A1 .Location in patent: Page/Page column 95
[2]Patent: US2005/148623,2005,A1 .Location in patent: Page/Page column 126

83
[ 854754-00-0 ]
[ 162537-11-3 ]
methyl (1S,4R,6S,7S,10S)-7-benzyl-1,10-ditert-butyl-6-hydroxy-2,9,12-trioxo-4-[4-(2-pyridinyl)benzyl]-13-oxa-3,8,11-triazatetradec-1-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; at 25℃; for 16h;	A solution of the product of Example 1H (0.18 g, 0.33 mmol) in THF (3.3 mL) was treated with the product of Example 1F (0.11 g, 0.60 mmol), DEPBT (0.15 g, 0.50 mmol), and N,N-diisopropylethylamine (0.29 mL, 1.66 mmol), stirred at 25 C. for 16 hours, and partitioned between ethyl acetate and 10% Na2CO3 solution. The organic phase phase was washed with additional 10% Na2CO3 solution and brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0%-75% ethyl acetate in chloroform to give the title product (0.19 g, 81% yield). 1H NMR (300 MHz, DMSO-d6), delta ppm 0.75 (s, 9H), 0.78 (s, 9H), 1.28 (m, 2H), 1.55 (m, 1H), 2.70 (m, 4H), 3.55 (d, J=1.77 Hz, 6H), 3.85 (m, 3H), 4.15 (m, 1H), 4.80 (d, J=5.15 Hz, 1H), 6.75 (d, J=9.19 Hz, 1H), 6.86 (d, J=9.56 Hz, 1H), 7.13 (m, 5H), 7.22 (d, J=8.46 Hz, 2H), 7.32 (m, 1H), 7.52 (d, J=8.82 Hz, 1H), 7.88 (m, 5H), 8.64 (d, J=4.41 Hz, 1H).

Reference： [1]Patent: US2005/131017,2005,A1 .Location in patent: Page/Page column 95

84
tert-butyl (1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate hydrochloride [ No CAS ]
[ 162537-11-3 ]
methyl (S)-1-((2S,4S,5S)-5-(tert-butoxycarbonyl)amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; at 25℃; for 16h;	A solution of the product of Example 2A (3.7 g, 7.4) in THF (75 mL) was treated with the product from Example 1F (1.39 g, 7.4 mmol), DEPBT (3.3 g, 11.0 mmol), and N,N-diisopropylethylamine (6.4 mL, 36.7 mmol), stirred at 25 C. for 16 hours, and partitioned between ethyl acetate and 10% Na2CO3 solution. The organic phase phase was washed with additional 10% Na2CO3 solution and brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 33%-100% ethyl acetate in chloroform to give the title compound (3.5 g, 75% yield).

Reference： [1]Patent: US2005/131017,2005,A1 .Location in patent: Page/Page column 95

85
[ 854754-04-4 ]
[ 162537-11-3 ]
dimethyl (2S,2'S)-1,1'-((2S,3S,5S)-3-hydroxy-1-phenyl-6-(4-(pyridin-2-yl)phenyl)hexane-2,5-diyl)bis(azanediyl)bis(3,3-dimethyl-1-oxobutane-2,1-diyl)dicarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; at 25℃; for 3h;	A solution of the product of Example 2C (1.6 g, 3.0 mmol) in THF (30 mL) was treated with the product of Example 1F (0.57 g, 3.0 mmol), DEPBT (1.35 g, 4.5 mmol), and N,N-diisopropylethylamine (2.6 mL, 14.9 mmol), stirred at 25 C. for 3 hours and partitioned between ethyl acetate and 10% Na2CO3 solution. The organic phase phase was washed with additional 10% Na2CO3 solution and brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 50% ethyl acetate in chloroform, followed by 5% methanol in chloroform to give the title compound (1.59 g, 75% yield). 1H NMR (300 MHz, DMSO-d6), delta ppm 0.79 (s, 9H), 0.82 (s, 9H), 1.51 (m, 2H), 2.72 (m, 3H), 3.49 (s, 3H), 3.55 (s, 3H), 3.63 (m, 1H), 3.82 (d, J=9.93 Hz, 1H), 3.90 (d, J=9.56 Hz, 1H), 4.04 (m, 3H), 4.86 (d, J=5.88 Hz, 1H), 6.60 (d, J=9.93 Hz, 1H), 6.78 (d, J=9.19 Hz, 1H), 7.16 (m, 7H), 7.31 (m, 1H), 7.54 (d, J=8.46 Hz, 1H), 7.83 (m, 5H), 8.63 (d, J=4.78 Hz, 1H).
75%	With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; at 25℃; for 3h;	EXAMPLE 2D methyl(1S,4S,5S,7S,10S)-4-benzyl-1,10-ditert-butyl-5-hydroxy-2,9,12-trioxo-7-[4-(2-pyridinyl)benzyl]-13-oxa-3,8,11-triazatetradec-1-ylcarbamate A solution of the product of Example 2C (1.6 g, 3.0 mmol) in THF (30 mL) was treated with the product of Example 1F (0.57 g, 3.0 mmol), DEPBT (1.35 g, 4.5 mmol), and N,N-diisopropylethylamine (2.6 mL, 14.9 mmol), stirred at 25 C. for 3 hours and partitioned between ethyl acetate and 10% Na2CO3 solution. The organic phase was washed with additional 10% Na2CO3 solution and brine, dried over MgSO4 filtered and concentrated. The residue was chromatographed on silica gel eluding with 50% ethyl acetate in chloroform, followed by. 5% methanol in chloroform to give the title compound (1.59g, 75% yield). 1H NMR (300 MHz, DMSO-d6), delta ppm 0.79 (s, 9 H), 0.82 (s, 9 H), 1.51 (m, 2 H), 2.51 (m, 1 H),2.72 (m, 3 H), 3.49 (s, 3 H), 3.55 (s, 3 H), 3.63 (m, 1 H), 3.82 (d, J=9.93 Hz, 1 H), 3.90 (d, J=9.56 Hz, 1 H), 4.04 (m, 2 H), 4.86 (d, J=5.88 Hz, 1 H), 6.60 (d, J=9.93 Hz, 1 H), 6.78 (d, J=9.19 Hz, 1 H), 7.16 (m, 7 H), 7.31 (m, 1 H), 7.54 (d, #8.46 Hz, 1 H), 7.83 (m, 5 H), 8.63 (d, J=4.78 Hz, 1 H).

Reference： [1]Patent: US2005/131017,2005,A1 .Location in patent: Page/Page column 96
[2]Patent: US2005/148623,2005,A1 .Location in patent: Page/Page column 127
[3]Journal of Medicinal Chemistry,2009,vol. 52,p. 2571 - 2586

86
[ 854754-06-6 ]
[ 162537-11-3 ]
[ 854754-07-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 0 - 25℃; for 2h;	A solution of the product of Example 3B (0.150 g, 0.276 mmol) in DMF (3 mL) were treated with the product of Example 1F (0.052 g, 0.275 mmol), EDAC (0.080 g, 0.417 mmol), HOBT (0.055, 0.407 mmol), and NMM (0.090 mL, 0.819 mmol) at 0 C., stirred at 25 C. for 2 hours, and partitioned between ethyl acetate and water. The organic phase was washed with 10% citric acid, diluted sodium bicarbonate, and brine, dried over MgSO4, filtered and concentrated. The concentrate was purified by reversed phase chromatography on a C18 column, eluting with a gradient starting with 5%-100% acetonitrile in water (0.1% TFA) to give the title compound (0.130 g, 70% yield).
70%		EXAMPLE 3C methyl(1S)-1-[((1S,3S,4S)-1-benzyl-4-[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-hydroxy-5-phenylpentyl)amino]carbonyl}-2,2-dimethylpropylcarbamate A solution of the product of Example 3B (0.150 g, 0.276 mmol) in DMF (3 mL) was treated with the product of Example 1F (0.052 g, 0.275 mmol), EDAC (0.080 g, 0.417 mmol), HOBT (0.055, 0.407 mmol), and NMM (0.090 mL, 0.819 mmol) at 0 C., stirred at 25 C. for 2 hours, and partitioned between ethyl acetate and water. The organic phase was washed with 10% citric acid, diluted sodium bicarbonate, and brine, dried over MgSO4, filtered and concentrated. The concentrate was purified by reversed phase chromatography on a C18 column, eluding with a gradient starting with 5%-100% acetonitrile in water (0.1% TFA) to give the title compound (0.130 g, 70% yield).

Reference： [1]Patent: US2005/131017,2005,A1 .Location in patent: Page/Page column 96
[2]Patent: US2005/148623,2005,A1 .Location in patent: Page/Page column 12

87
C₃₃H₄₅N₅O₄S [ No CAS ]
[ 162537-11-3 ]
methyl (1S)-1-[((1S,3S,4S)-1-benzyl-3-hydroxy-4-[(2S)-2-(3-[2-(methoxymethyl)-1,3-thiazol-4-yl]methyl}-2-oxo-1-imidazolidinyl)-3,3-dimethylbutanoyl]amino}-5-phenylpentyl)amino]carbonyl}-2,2-dimethylpropylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 0 - 25℃; for 16h;	A solution containing the product from Example 61 (0.047 g, 0.066 mmol) in dichloromethane (1 mL) was treated with trifluoroacetic acid (1 mL), stirred at 25 C. for 1 hour, concentrated, and partitioned between ethyl acetate and saturated NaHCO3. The organic phase phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the residue (0.030 g, 0.049 mmol) in DMF (0.5 mL) was treated with the product from Example 1F (0.010 g, 0.053 mmol), EDAC (0.020 g, 0.104 mmol), HOBT (0.015 g, 0.111 mmol), and NMM (0.016 mL, 0.146 mmol) at 0 C., stirred at 25 C. for 16 hours, and partitioned between ethyl acetate and water. The organic phase phase was washed with 10% citric acid, diluted sodium bicarbonate, and brine, and dried over MgSO4, filtered and concentrated. The residue was purified by reversed phase chromatography on a C18 column, eluting with 5-100% acetonitrile in water (0.1% TFA) to give the title compound (0.031 g, 79% yield). 1H NMR (300 MHz, DMSO-d6), delta ppm 0.82 (s, 9H), 0.89 (s, 9H), 1.25 (m, 1H), 1.50 (m, 2H), 2.37 (m, 1H), 2.65 (d, J=7.35 Hz, 2H), 2.73 (d, J=9.56 Hz, 1H), 3.02 (m, 2H), 3.19 (m, 1H), 3.38 (s, 3H), 3.55 (s, 3H), 3.85 (m, 3H), 4.08 (m, 3H), 4.38 (m, 2H), 4.68 (s, 2H), 6.61 (d, J=9.93 Hz, 1H), 7.08 (m, 10H), 7.43 (m, 2H), 7.74 (d, J=8.46 Hz, 1H).
79%		EXAMPLE 6J methyl(1S)-1-[((1S,3S,4S)-1-benzyl-3-hydroxy-4-[(2S)-2-(3-[2-(methoxymethyl)-1,3-thiazol-4-yl]methyl}-2-oxo-1-imidazolidinyl)-3,3-dimethylbutanoyl]amino}-5-phenylpentyl)amino]carbonyl}-2,2-dimethylpropylcarbamate A solution containing the product from Example 61 (0.047 g, 0.066 mmol) in dichloromethane (1 mL) was treated with trifluoroacetic acid (1 mL), stirred at 25 C. for 1 hour, concentrated, and partitioned between ethyl acetate and saturated NaHCO3. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the residue (0.030 g, 0.049 mmol) in DMF (0.5 mL) was treated with the product from Example 1F (0.010 g, 0.053 mmol), EDAC (0.020 g, 0.104 mmol), HOBT (0.015 g, 0.111 mmol), and NMM (0.016 mL, 0.146 mmol) at 0 C., stirred at 25 C. for 16 hours, and partitioned between ethyl acetate and water. The organic phase was washed with 10% citric acid, diluted sodium bicarbonate, and brine, and dried over MgSO4, filtered and concentrated. The residue was purified by reversed phase chromatography on a C18 column, eluding with 5-100% acetonitrile in water (0.1% TFA) to give the title compound (0.031 g, 79% yield). 1H NMR (300 MHz, DMSO-d6), delta ppm 0.82 (s, 9 H), 0.89 (s, 9 H), 1.25 (m, 1 H), 1.50 (m, 2 H), 2.37 (m, 1H), 2.65 (d, J=7.35 Hz, 2 H), 2.73 (d, J=9.56 Hz, 1 H), 3.02 (m, 2 H), 3.19 (m, 1 H), 3.38 (s, 3 H), 3.55 (s, 3 H), 3.85 (m, 3 H), 4.08 (m, 3 H), 4.38 (m, 2 H), 4.68 (s, 2 H), 6.61 (d, J=9.93 Hz, 1 H), 7.08 (m, 10 H), 7.43 (m, 2 H), 7.74 (d, J=8.46 Hz, 1 H).

Reference： [1]Patent: US2005/131017,2005,A1 .Location in patent: Page/Page column 100
[2]Patent: US2005/148623,2005,A1 .Location in patent: Page/Page column 133

88
C₃₄H₄₅N₅O₃ [ No CAS ]
[ 162537-11-3 ]
methyl (1S)-1-[({(1S,3S,4S)-1-benzyl-3-hydroxy-4-[((2S, 3S)-3-methyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2-oxo-1-imidazolidinyl}pentanoyl)amino]-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%		EXAMPLE 7D methyl(1S)-1-[({(1S,3S,4S)-1-benzyl-3-hydroxy-4-[((2S)-3-methyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2-oxo-1-imidazolidinyl}pentanoyl)amino]-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate A solution containing the product from Example 7C (0.080 g, 0.119 mmol) in dichloromethane (1 mL) was treated with trifluoroacetic acid (1 mL), stirred at 25 C. for 1 hour and concentrated. The concentrate was partitioned between ethyl acetate and saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. A solution of the residue (0.056 g, 0.098 mmol) in DMF (1 mL) was treated with the product from Example 1F (0.020 g, 0.106 mmol), EDAC (0.030 g, 0.156 mmol), HOBT (0.020 g, 0.148 mmol), and NMM (0.030 mL, 0.273 mmol) at 0 C., stirred at 25 C. for 16 hours, and partitioned between ethyl acetate and water. The organic phase was washed with 10% citric acid, dilute sodium bicarbonate, and brine, and dried over MgSO4, filtered and concentrated. The residue was purified by reversed phase chromatography on a C18 column, eluding with 5-100% acetonitrile in water (0.1% TFA) to give the title compound (0.049 g, 67% yield). 1H NMR (300 MHz, DMSO-d6), delta ppm 0.79 (m, 15 H), 0.93 (m, 2 H), 1.31 (m, 1 H), 1.50 (m, 2 H), 1.82 (m, 1 H), 2.45 (s, 3 H), 2.67 (m, 4 H), 3.06 (m, 3 H), 3.55 (s, 3 H), 3.64 (m, 1 H), 3.82 (d, J=9.93 Hz, 1 H), 3.93 (d, J=11.03 Hz, 1 H), 4.13 (m, 2 H), 4.35 (s, 2 H), 4.64 (d, J=7.35 Hz, 1 H), 6.62 (d, J=9.93 Hz, 1 H), 7.02 (d, J=7.72 Hz, 1 H), 7.13 (m, 11 H), 7.26 (d, J=9.93 Hz, 1 H), 7.66 (t, J=7.72 Hz, 1 H), 7.75 (d, J=8.46 Hz, 1 H).
	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 0 - 25℃; for 16h;	A solution containing the product from Example 7C (0.080 g, 0.119 mmol) in dichloromethane (1 mL) was treated with trifluoroacetic acid (1 mL), stirred at 25 C for 1 hour and concentrated. The concentrate was partitioned between ethyl acetate and saturated NaHCO3. The organic phase phase was washed with brine, dried over MgSO4, filtered and concentrated. A solution of the residue (0.056 g, 0.098 mmol) in DMF (1 mL) was treated with the product from Example 1F (0.020 g, 0.106 mmol), EDAC (0.030 g, 0.156 mmol), HOBT (0.020 g, 0.148 mmol), and NMM (0.030 mL, 0.273 mmol) at 0 C., stirred at 25 C. for 16 hours, and partitioned between ethyl acetate and water. The organic phase phase was washed with 10% citric acid, dilute sodium bicarbonate, and brine, and dried over MgSO4 filtered and concentrated. The residue was purified by reversed phase chromatography on a C18 column, eluting with 5-100% acetonitrile in water (0.1% TFA) to give the title compound (0.049 g, 67% yield). 1H NMR (300 MHz, DMSO-d6), delta ppm 0.79 (m, 15H), 0.93 (m, 2H), 1.31 (m, 1H), 1.50 (m, 2H), 1.82 (m, 1H), 2.45 (s, 3H), 2.67 (m, 4H), 3.06 (m, 3H), 3.55 (s, 3H), 3.64 (m, 1H), 3.82 (d, J=9.93 Hz, 1H), 3.93 (d, J=11.03 Hz, 1H), 4.13 (m, 2H), 4.35 (s, 2H), 4.64 (d, J=7.35 Hz, 1H), 6.62 (d, J=9.93 Hz, 1H), 7.02 (d, J=7.72 Hz, 1H), 7.13 (m, 11H), 7.26 (d, J=9.93 Hz, 1H), 7.66 (t, J=7.72 Hz, 1H), 7.75 (d, J=8.46 Hz, 1H).

Reference： [1]Patent: US2005/148623,2005,A1 .Location in patent: Page/Page column 133-134
[2]Patent: US2005/131017,2005,A1 .Location in patent: Page/Page column 100; 101

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P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 162537-11-3 ] {[proInfo.proName]}

Quality Control of [ 162537-11-3 ]

Related Doc. of [ 162537-11-3 ]

Product Details of [ 162537-11-3 ]

Calculated chemistry of [ 162537-11-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 162537-11-3 ]

Application In Synthesis of [ 162537-11-3 ]

[ 162537-11-3 ] Synthesis Path-Upstream 1~2

[ 162537-11-3 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 162537-11-3 ]

Amino Acid Derivatives

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 162537-11-3 ]