[ CAS No. 128595-07-3 ] {[proInfo.proName]}

Name: 128595-07-3|N-(Cyclopentyloxycarbonyloxy)succinimide|98%
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SKU: A135588
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Quality Control of [ 128595-07-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 128595-07-3 ]

Product Details of [ 128595-07-3 ]

CAS No. :	128595-07-3	MDL No. :	MFCD04038113
Formula :	C₁₀H₁₃NO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MKHDXOXWZKDUKB-UHFFFAOYSA-N
M.W :	227.21	Pubchem ID :	15927743
Synonyms :

Calculated chemistry of [ 128595-07-3 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.7
Num. rotatable bonds :	4
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.93
TPSA :	72.91 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.9
Log Po/w (XLOGP3) :	0.9
Log Po/w (WLOGP) :	0.77
Log Po/w (MLOGP) :	0.64
Log Po/w (SILICOS-IT) :	0.45
Consensus Log Po/w :	0.93

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.55
Solubility :	6.38 mg/ml ; 0.0281 mol/l
Class :	Very soluble
Log S (Ali) :	-2.02
Solubility :	2.19 mg/ml ; 0.00963 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.7
Solubility :	45.5 mg/ml ; 0.2 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.5

Safety of [ 128595-07-3 ]

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

Application In Synthesis of [ 128595-07-3 ]

* 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 [ 128595-07-3 ]
Downstream synthetic route of [ 128595-07-3 ]

[ 128595-07-3 ] Synthesis Path-Upstream 1~1

1
[ 74124-79-1 ]
[ 96-41-3 ]
[ 128595-07-3 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 1, p. 110 - 115
[2] Synlett, 2011, # 10, p. 1454 - 1458

[ 128595-07-3 ] Synthesis Path-Downstream 1~33

1
[ 74124-79-1 ]
[ 96-41-3 ]
[ 128595-07-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 110 - 115
[2]Synlett,2011,p. 1454 - 1458

2
[ 128595-07-3 ]
[ 116586-35-7 ]
[ 116587-24-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 110 - 115

3
[ 128595-07-3 ]
N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-amino-4(S)-hydroxy-6-phenyl-2(R)-(phenylmethyl)-hexanoic amide [ No CAS ]
[(1S,2S,4R)-1-Benzyl-2-hydroxy-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-carbamic acid cyclopentyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 292 - 294

4
[ 128595-07-3 ]
[ 169280-56-2 ]
Amprenavir [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,1999,vol. 38,p. 1931 - 1934

5
[ 128595-07-3 ]
[ 192800-79-6 ]
{(1S,2S)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid cyclopentyl ester [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,1999,vol. 38,p. 1931 - 1934

6
C₃₅H₃₆N₄O₇ [ No CAS ]
[ 128595-07-3 ]
2-(7-methoxy-2-phenyl-quinolin-4-yloxy)-9-methyl-7-methylene-5-(4-methyl-pentanoylammo)-4,16-dioxo-1,2,3,4,5,6,7,11,12,13,14,15,16,16a-tetradecahydro-10-oxa-3a,15-diaza-cyclopentacvclopentadecene-14-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃; for 3 - 4h;	Synthesis of 2-(7-Methoxy-2 -phenyl-quinolin-4-yloxy)-9-methyl-7-methylene-5-(4-methyl- pentanoylammo)-4,16-dioxo-l,2,3A5,6,7,l 1,12,13, 14,15,16 ,16a-tetradecahydro-10-oxa- 3a,15-diaza-cyclopentacvclopentadecene-14-carboxylic acid (Ex. 16); Amine Ex. 16 EPO <DP n="94"/>TABLE 3Reagent MW EQ g/mL mmolAmine 624.7 1.0 6 mg 0.0096Cyclopentyloxycarbonylsuccinimide 227 1.0 2.4 mg 0.0096 TEA 101 4.0 6 uL 0.04THF 40O uLTypical Procedure using succinimides to make carbamates[00130] A solution of <strong>[128595-07-3]N-(cyclopentyloxycarbonyloxy)succinimide</strong> (2.4 mg, 0.0096 mmol) in THF (400 uL) was added to an amine (6 mg, 0.0096 mmol) followed by addition of TEA (6 uL, 0.04 mmol) at room temperature. The reaction was monitored by HPLC and LCMS. After shaking for 3-4 hours at room temperature, the solution was evaporated to dryness and dissolved in NMP (300 uL). The entire reaction was filtered and injected onto a prepatory HPLC reverse phase column. The proper fractions were collected and lyophilized to provide 3-4 mg of product as a powder in high purity.

Reference： [1]Patent: WO2007/1406,2007,A2 .Location in patent: Page/Page column 92-93

7
C₃₃H₃₇BrF₂N₃O₁₁PS [ No CAS ]
[ 128595-07-3 ]
[ 1001096-38-3 ]

Yield	Reaction Conditions	Operation in experiment
96%		To a solution of cyclic olefin (1.48 g, 1.67 mmol) in CH2Cl2 (10 mL) was added 4 N HCl in 1 ,4- dioxane (6.26 mL, 25.05 mmol). The reaction mixture was stirred at r.t. for 3.5 h, concentrated, dried under vacuum overnight, and then dissolved in THF (14.3 mL) / H2O (2.4 mL). Compound Carbonic acid cyclopentyl ester 2,5-dioxo-pyrrolidin-l -yl ester (398 mg, 1.75 mmol) and TEA (0.7 mL, 5.01 mmol) were added. The reaction was stirred at r.t. for 2 h and additional Carbonic acid cyclopentyl ester 2,5-dioxo-pyrrolidin-l-yl ester (38 mg) was added. The reaction was stirred for 2 h. The reaction was quenched by adding 0.5 N HCl and diluted with EtOAc. The two layers were separated. The organic layers were washed with 0.5 N HCl and brine, dried with Na2SO4, and concentrated. The crude product was purified by combi-flash to give 1.45 g of cyclopentyl carbarmate in 96% yield. 31P NMR (121.4 MHz, CDCl3) delta 44.4, 43.1. LC/MS = 902.0 (M++l).

Reference： [1]Patent: WO2008/5565,2008,A2 .Location in patent: Page/Page column 210

8
[ 20859-02-3 ]
[ 128595-07-3 ]
[ 572924-00-6 ]

Yield	Reaction Conditions	Operation in experiment
79%		[00277] In a 5L RB flask dissolved t-butyl glycine (74 g, 0.56 mol, 1.02 eq.) in saturated sodium bicarbonate (11 vol). Cyclopentyl 2,5-dioxopyrrolidin-l-yl carbonate (126 g, 0.55 mol, 1 eq.) was dissolved in acetone (5.5 vol) and the solution slowly added via addition funnel at room temperature to the solution of the glycine. The reaction mixture was stirred at room temperature until complete (approximately 4 hours). The acetone was removed under reduced pressure and the remaining aqueous solution was extracted with 30% ethyl acetate in hexanes (thrice, 5.5 vol each). The organic layers were discarded. The pH of EPO <DP n="293"/>the aqueous layer was adjusted to 2 with 2 N HCl and then extracted with ethyl acetate(thrice, 5.5 vol). The combined organic layers were dried (Na2SO4), filtered, and the solvent removed under reduced pressure to provide a clear oil the slowly crystallized. The crude product was crystallized from hexanes/ethyl acetate to provide (S)-2- (cyclopentyloxycarbonylamino)-3,3-dimethylbutanoic acid as a white solid (82 g). The mother liquid was stripped and a second crop of crystals obtained (combined yield 105.54 g, 79% yield).
	With triethylamine; In tetrahydrofuran; water; at 18 - 22℃; for 2.5h;	THF (350 mL) was added to a flask containing carbonic acid cyclopentyl ester 2,5- DIOXO-PYRROLIDIN-1-YL ester (9.00 g; 39.6 MMOL) and TERT-BUTYL GLYCINE (6.24 g; 47.5 MMOL) resulting in a suspension. Distilled water (100 mL) was added with vigorous stirring. A small amount of solid remained undissolved. Triethylamine (16.6 mL; 119 MMOL) was then added resulting in a homogenous solution which was stirred at R. T. After 2.5 h, the THF was evaporated and the aqueous residue diluted with water (100 mL). The reaction was rendered basic by the addition of 1 N NAOH (25 ML-FINAL pH >10). The solution was washed with EtOAc (2X 200 mL) and the aqueous phase acidified with 1 N HCI (ca. 70 mL-final pH <2). The turbid solution was extracted with EtOAc (200 + 150 mL). The extract was dried (MGS04) and evaporated to give carbamate 4a as a white solid (8.68 g).
	With triethylamine; In tetrahydrofuran; water; at 20℃; for 2.5h;	THF (350 mL) was added to a flask containing <strong>[128595-07-3]carbonic acid cyclopentyl ester 2,5-dioxo-pyrrolidin-1-yl ester</strong> (9.00 g; 39.6 mmol) and tert-butyl glycine (6.24 g; 47.5 mmol) resulting in a suspension. Distilled water (100 mL) was added with vigorous stirring. A small amount of solid remained undissolved. Triethylamine (16.6 mL; 119 mmol) was then added resulting in a homogenous solution which was stirred at R.T. After 2.5 h, the THF was evaporated and the aqueous residue diluted with water (100 mL). The reaction was rendered basic by the addition of 1 N NaOH (25 mL-final pH >10). The solution was washed with EtOAc (2×200 mL) and the aqueous phase acidified with 1 N HCl (ca. 70 mL-final pH <2). The turbid solution was extracted with EtOAc (200+150 mL). The extract was dried (MgSO4) and evaporated to give carbamate 2a as a white solid (8.68 g).

	With triethylamine; In tetrahydrofuran; water; at 20℃; for 2.5h;	The P3 carbamate fragment 1a was prepared as described in WO 03/064416. THF(350mL) was added to a flask containing <strong>[128595-07-3]carbonic acid cyclopentyl ester 2,5-dioxo-pyrrolidin-1-yl ester</strong> (Q.OOg; 39.6mmol) and terf-butyl glycine (6.24g; 47.5mmol)resulting in a suspension. Distilled water (100mL) was added with vigorous stirring. Asmall amount of solid remained undissolved. Triethylamine (16.6ml 119mmol) wasthen added resulting in a homogenous solution which was stirred at R.T. After 2.5h,the THF was evaporated and the aqueous residue diluted with water (100ml_). Thereaction was rendered basic by the addition of 1 N NaOH (25mL - final pH >10). Thesolution was washed with EtOAc (2 x 200ml_) and the aqueous phase acidified with 1N HCI (ca. 70ml final pH <2). The turbid solution was extracted with EtOAc (200 + 150mL). The extract was dried (MgSO4) and evaporated to give carbamate 1a as a white solid (8.68g).
		[0312] In a 5L RB flask dissolved t-butyl glycine (74 g, 0.56 mol, 1.02 eq.) in saturated sodium bicarbonate (11 vol). Cyclopentyl 2,5-dioxopyrrolidin-l-yl carbonate (126 g, 0.55 mol, 1 eq.) was dissolved in acetone (5.5 vol) and the solution slowly added via addition funnel at room temperature to the solution of the glycine. The reaction mixture was stirred at room temperature until complete (approximately 4 hours). The acetone was removed under reduced pressure and the remaining aqueous solution was extracted with 30% ethyl acetate in hexanes (thrice, 5.5 vol each). The organic layers were discarded. The pH of the aqueous layer was adjusted to 2 with 2 N HCl and then extracted with ethyl acetate (thrice, 5.5 vol). The combined organic layers were dried (Na2SO4), filtered, and the solvent removed under reduced pressure to provide a clear oil the slowly crystallized. The crude product was crystallized from hexanes/ethyl acetate to provide (S)-2-(cyclopentyloxycarbonylamino)-3,3- dimethylbutanoic acid as a white solid (82 g). The mother liquid was stripped and a second crop of crystals obtained (combined yield 105.54 g).

Reference： [1]Patent: WO2007/25307,2007,A2 .Location in patent: Page/Page column 291-292
[2]Patent: WO2004/103996,2004,A1 .Location in patent: Page 35-36
[3]Patent: US2004/229818,2004,A1 .Location in patent: Page/Page column 16
[4]Patent: WO2006/85,2006,A1 .Location in patent: Page/Page column 72-73
[5]Journal of Medicinal Chemistry,2010,vol. 53,p. 6466 - 6476
[6]Synlett,2011,p. 1454 - 1458
[7]Patent: WO2008/106139,2008,A1 .Location in patent: Page/Page column 461

9
[ 128595-07-3 ]
[ 572924-00-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tert-butylaminoacetic acid; sodium hydrogencarbonate; acetone;	Preparation of (S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoic acid In a 5 L RB flask dissolved t-butyl glycine (74 g, 0.56 mol, 1.02 eq.) in saturated sodium bicarbonate (11 vol). Cyclopentyl 2,5-dioxopyrrolidin-1-yl carbonate (126 g, 0.55 mol, 1 eq.) was dissolved in acetone (5.5 vol) and the solution slowly added via addition funnel at room temperature to the solution of the glycine. The reaction mixture was stirred at room temperature until complete (approximately 4 hrs). The acetone was removed under reduced pressure and the remaining aqueous solution was extracted with 30% ethyl acetate in hexanes (thrice, 5.5 vol each). The organic layers were discarded. The pH of the aqueous layer was adjusted to 2 with 2 N HCl and then extracted with ethyl acetate (thrice, 5.5 vol). The combined organic layers were dried (Na2SO4), filtered, and the solvent removed under reduced pressure to provide a clear oil the slowly crystallized. The crude product was crystallized from hexanes/ethyl acetate to provide (S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoic acid as a white solid (82 g). The mother liquid was stripped and a second crop of crystals obtained (combined yield 105.54 g).

Reference： [1]Patent: US2010/272681,2010,A1

10
N-(4-(7-(azetidin-3-ylethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide trifluoroacetic acid salt [ No CAS ]
[ 128595-07-3 ]
[ 1426688-43-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;	EXAMPLE 10 Alternative Preparation of a Compound of Formula I A. Preparation of a Compound of Formula I in which R1 is Cyclopentylazetidin-1- carboxylate, R2 is Methyl, and R3 is Hydro en To a mixture of N-(4-(7-(azetidin-3-ylethynyl)-4-oxo-4H-chromen-3- yl)phenyl)methanesulfonamide.trifluoroacetic acid salt (55 mgs, 0.140 mmol) in dichloromethane (3 mL) was added cyclopentyl 2,5-dioxopyrrolidin-l-yl carbonate (95 mgs, 0.42 mmol) and diisopropylethylamine (0.2 mL, 1.4 mmol), and the mixture was stirred at room temperature for 16 hours. The resulting mixture was concentrated. under reduced pressure, and chromatographed (Si02, 25% ethyl acetate/dichloromethane) to provide cyclopentyl-3-((3-(4-(methylsulfonamido (phenyl )- 4-oxo-4H-chromen-7-yl)ethynyl)azetidine- 1 -carboxylate: MS found for C27H26 206S as (M+H)+ 507.07 1H NMR (400MHz, dmso-d6): delta: 9.85 (s, 1H); 8.53 (s, 1H); 8.11 (d, J = 8.4 Hz, 1H); 7.56 (s, 1H); 7.54-7.51 (m, 3H); 7.26 (d, J = 8.4 Hz, 2H), 4.96 (m, 1H); 4.23-4.19 (m, 2H); 3.94-3.90 (m, 2H); 3.79-3.74 (m, 1H); 3.01 (s, 3H), 1.78-1.50 (m, 8H).

Reference： [1]Patent: WO2013/33377,2013,A1 .Location in patent: Page/Page column 45; 46

11
C₃₂H₄₂N₆O₇S*ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R,6S,13aS,4aR,16aS,Z)-14a-((cyclopropylsulfonyl)carbamoyl)-2-((3-ethyl-7-methoxyquinoxalin-2-yl)oxy)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 36h;Inert atmosphere;	A solution of the above amine salt 20a (0.37 g, 0.53 mmol) in anhydrous CH3CN (15 mL) was treated with DIEA (0.35 mL, 2.1 mmol) and <strong>[128595-07-3]N-(cyclopentyloxycarbonyloxy)-succinimide</strong> (0.15 g, 0.66 mmol). The reaction mixture was stirred at room temperature for 36 h, thenconcentrated under reduced pressure and dried under high vacuum. The residue was purified by flash chromatography using 50-90% EtOAc/hexanes as the eluent to provide the target compound 22a (0.32 g, 79%) as a white solid. NMR (400 MHz, CDCI3) delta 10.29 (s, 1 H), 7.83 (d, J= 9.6 Hz, 1 H), 7.21-7.16 (m, 2 H), 6.94 (s, 1 H), 5.93 (br s, 1 H), 5.70 (q, J= 8.8 Hz, 1 H), 5.26 (d, J= 8.0 Hz, 1 H), 4.96 (t, J= 8.4 Hz, 1 H), 4.86-4.82 (m, 1 H), 4.60 (t, J= 7.6 Hz, 1 H), 4.45 (d, J= 11.2 Hz, 1 H), 4.34-4.28 (m, 1 H), 4.03 (dd, J= 11.2, 4.0 Hz, 1 H), 3.94 (s, 3 H), 2.93-2.85 (m, 3 H), 2.70-2.48 (m, 3 H), 2.30 (q, J= 8.8 Hz, 1 H), 1.93-1.23 (m, 23 H), 1.15-1.06 (m, 2 H), 0.96-0.88 (m, 1 H) ppm;13C NMR (100 MHz, CDCI3) delta 177.18, 173.03, 168.04, 160.28, 155.65, 154.93, 148.78, 140.90, 136.27, 134.20, 128.92, 124.46, 118.80, 105.92, 77.87, 74.55, 59.47, 55.72, 53.01, 52.17, 44.54, 34.58, 32.72, 32.63, 32.59, 31.01, 29.70, 27.14, 27.05, 26.40, 26.05, 23.56, 22.16, 20.90, 11.61, 6.67, 6.12 ppm; HRMS (ESI) m/z: [M + H]+calcd for CssHsiNeOgS, 767.3433; found 767.3408. Anal. HPLC: kappa 14.50 min, purity 98%.

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716
[2]Patent: WO2018/236928,2018,A1 .Location in patent: Paragraph 00175; 00176

12
C₃₃H₄₄N₆O₇S*ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R,6S,13aS,14aR,16aS,Z)-2-((3-ethyl-7-methoxyquinoxalin-2-yl)oxy)-14a-(((1-methylcyclopropyl)sulfonyl)-carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716

13
C₃₁H₄₀N₆O₇S*ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R,6S,13aS,14aR,16aS,Z)-14a-((cyclopropylsulfonyl)carbamoyl)-2-((7-methoxy-3-methylquinoxalin-2-yl)oxy)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 36h;Inert atmosphere;	A solution of the above amine salt 20b (0.29 g, 0.43 mmol) in anhydrous CH3CN (13 mL) was treated with DIEA (0.28 mL, 1.7 mmol) and <strong>[128595-07-3]N-(cyclopentyloxycarbonyloxy)-succinimide</strong> (0.108 g, 0.48 mmol). The reaction mixture was stirred at room temperature for 36 h, then concentrated under reduced pressure and dried under high vacuum. The residue was purified by flash chromatography using 50-90% EtOAc/hexanes as the eluent to provide the target compound 22b (0.29 g, 90%) as a white solid. NMR (400 MHz, CDC13) delta 10.29 (s, 1 H), 7.79 (d, J= 9.6 Hz, 1 H), 7.20-7.16 (m, 2 H), 6.98 (s, 1 H), 5.91 (br s, 1 H), 5.68 (q, J= 8.8 Hz, 1 H), 5.24 (d, J= 8.0 Hz, 1 H), 4.96 (t, J= 8.8 Hz, 1 H), 4.88-4.84 (br s, 1 H), 4.62 (t, J= 7.6 Hz, 1 H), 4.42 (d, J= 11.6 Hz, 1 H), 4.33-4.27 (m, 1 H), 4.04 (dd, J= 11.6, 4.0 Hz, 1 H), 3.94 (s, 3 H), 2.94-2.86 (m, 1 H), 2.69-2.48 (m, 5 H), 2.29 (q, J= 8.4 Hz, 1 H), 1.93-1.23 (m, 21 H), 1.17-1.05 (m, 2 H), 0.96-0.87 (m, 1 H) ppm; 13C NMR (100 MHz, CDCI3) delta 177.18, 173.03, 168.05, 160.22, 155.69, 155.32, 144.67, 140.95, 136.25, 134.26, 128.85, 124.44, 118.79, 105.97, 77.89, 74.63, 59.45, 55.72, 53.02, 52.20, 44.51, 34.55, 32.72, 32.65, 32.59, 31.02, 29.74, 27.21, 27.03, 26.04, 23.60, 23.57, 22.15, 20.90, 19.86, 6.67, 6.12 ppm; HRMS (ESI) m/z: calcd for C37H49N6O9S [M + H]+ 753.3276; found 753.3252. Anal. HPLC: fe 13.05 mm, purity 99%.

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716
[2]Patent: WO2018/236928,2018,A1 .Location in patent: Paragraph 00223; 00224

14
(2R,6S,13aS,4aR,16aS,Z)-6-amino-2-((7-methoxy-3-methylquinoxalin-2-yl)oxy)-N-((1-methylcyclopropyl)sulfonyl)-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide hydrochloride [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R,6S,13aS,14aR,16aS,Z)-2-((7-methoxy-3-methylquinoxalin-2-yl)oxy)-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716

15
C₃₀H₃₇ClN₆O₇S*ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R,6S,13aS,14aR,16aS,Z)-2-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)-14a-((cyclopropylsulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716

16
C₃₁H₃₉ClN₆O₇S*ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R,6S,13aS,14aR,16aS,Z)-2-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716

17
C₃₃H₄₄N₆O₇S*ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R,6S,13aS,14aR,16aS,Z)-14a-((cyclopropylsulfonyl)carbamoyl)-2-((3-isopropyl-7-methoxyquinoxalin-2-yl)oxy)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716

18
C₃₄H₄₆N₆O₇S*ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R,6S,13aS,14aR,16aS,Z)-2-((3-isopropyl-7-methoxyquinoxalin-2-yl)oxy)-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716

19
C₃₃H₃₈N₆O₆S₂*ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R,6S,13aS,14aR,16aS,Z)-14a-((cyclopropylsulfonyl)carbamoyl)-5,16-dioxo-2-((3-(thiophen-2-yl)quinoxalin-2-yl)oxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716

20
C₃₁H₄₀N₆O₆S*ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R,6S,13aS,14aR,16aS,Z)-14a-((cyclopropylsulfonyl)carbamoyl)-2-((3-ethylquinoxalin-2-yl)oxy)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716

21
C₃₁H₃₇F₃N₆O₇S*ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R, 6S,13aS,14aR,16aS, Z)-14a-((cyclopropylsulfonyl)carbamoyl)-2-((7-methoxy-3-(trifluoromethyl)quinoxalin-2-yl)oxy)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 24h;Inert atmosphere;	A solution of the above amine salt 20d (0.37 g, 0.52 mmol) in anhydrous CH3CN (15 mL) was treated with DIEA (0.35 mL, 2.1 mmol) and <strong>[128595-07-3]N-(cyclopentyloxycarbonyloxy)-succinimide</strong> (0.15 g, 0.66 mmol). The reaction mixture was stirred at room temperature for 24 h, thenconcentrated under reduced pressure and dried under high vacuum. The residue was purified by flash chromatography using 50-90% EtOAc/hexanes as the eluent to provide the target compound 22d (0.30 g, 74%) as a white solid. NMR (400 MHz, CDCI3) delta 10.27 (s, 1 H), 7.82 (d, J= 9.2 Hz, 1 H), 7.48 (dd, J= 9.2, 2.8 Hz, 1 H), 7.42 (d, J= 2.8 Hz, 1 H), 6.78 (s, 1 H), 5.95 (s, 1 H), 5.70 (q, J = 9.6 Hz, 1 H), 5.23 (d, J= 8.0 Hz, 1 H), 4.98 (t, J= 8.8 Hz, 1 H), 4.74-4.69 (m, 1 H), 4.60 (t, J= 7.6, 1 H), 4.54 (d, J= 11.6, 1 H), 4.25-4.19 (m, 1 H), 3.99 (dd, J= 11.6, 4.0 Hz, 1 H), 3.94 (s, 3 H), 2.94-2.88 (m, 1 H), 2.68-2.50 (m, 3 H), 2.31 (q, J= 8.8 Hz, 1 H), 1.94-1.24 (m, 21 H), 1.20-1.07 (m, 2 H), 0.96-0.89 (m, 1 H) ppm;13C NMR (100 MHz, CDCI3) delta 177.33, 173.29, 168.27, 159.68, 155.87, 152.08, 138.56, 137.24, 136.47, 134.74 (q, J= 36.0 Hz), 128.24, 125.75, 124.79, 120.87 (d, J = 273.2 Hz), 107.62, 78.02, 75.70, 59.68, 56.11, 52.90, 52.35, 44.83, 34.71, 32.92, 32.81, 32.64, 31.26, 29.87, 27.27, 26.24, 23.81, 23.75, 22.49, 21.11, 6.89, 6.34 ppm; HRMS (ESI) m/z: [M + H]+ calcd for C37H46F3N6O9S, 807.2994; found 807.2976. Anal. HPLC: fe 14.98 mm, purity 99%.

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716
[2]Patent: WO2018/236928,2018,A1 .Location in patent: Paragraph 00187; 00188

22
C₃₂H₃₉F₃N₆O₇S*ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((2R,6S,13aS,14aR,16aS,Z)-2-((7-methoxy-3-(trifluoromethyl)quinoxalin-2-yl)oxy)-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5699 - 5716

23
C₃₁H₄₂N₆O₇S*(x)ClH [ No CAS ]
[ 128595-07-3 ]
cyclopentyl ((S)-1-((2S,4R)-2-(((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)-4-((3-ethyl-7-methoxyquinoxalin-2-yl)oxy)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)carbamate [ No CAS ]