[ CAS No. 63128-51-8 ] {[proInfo.proName]}

Name: 63128-51-8|5-(tert-Butoxy)-5-oxopentanoic acid|95%
Brand: Ambeed
SKU: A608916
Price: 5.0 USD
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Quality Control of [ 63128-51-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 63128-51-8 ]

Product Details of [ 63128-51-8 ]

CAS No. :	63128-51-8	MDL No. :	MFCD09759103
Formula :	C₉H₁₆O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VZHNAVSRNGLHRD-UHFFFAOYSA-N
M.W :	188.22	Pubchem ID :	11424021
Synonyms :

Calculated chemistry of [ 63128-51-8 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.78
Num. rotatable bonds :	6
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.47
TPSA :	63.6 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.94
Log Po/w (XLOGP3) :	0.89
Log Po/w (WLOGP) :	1.58
Log Po/w (MLOGP) :	1.25
Log Po/w (SILICOS-IT) :	1.11
Consensus Log Po/w :	1.35

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.17
Solubility :	12.7 mg/ml ; 0.0673 mol/l
Class :	Very soluble
Log S (Ali) :	-1.81
Solubility :	2.91 mg/ml ; 0.0155 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.37
Solubility :	8.03 mg/ml ; 0.0427 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Safety of [ 63128-51-8 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338	UN#:	3265
Hazard Statements:	H318	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 63128-51-8 ]

* 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.

Downstream synthetic route of [ 63128-51-8 ]

[ 63128-51-8 ] Synthesis Path-Downstream 1~88

1
[ 63128-51-8 ]
[ 110-94-1 ]
[ 115-11-7 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1944,vol. 63,p. 189

2
[ 1070-62-8 ]
[ 75-65-0 ]
[ 63128-51-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1977,vol. No.6,p. 897 - 903

3
[ 64-69-7 ]
[ 1663-39-4 ]
[ 63128-51-8 ]

Reference： [1]Tetrahedron,1993,vol. 49,p. 8465 - 8470

4
[ 108-55-4 ]
[ 75-65-0 ]
[ 63128-51-8 ]

Yield	Reaction Conditions	Operation in experiment
46%	With zinc(II) chloride; at 60℃;Inert atmosphere;	ZnCl2 (4.77 mmol, 0.65 g) and glutaric anhydride (30.93 mmol, 3.53 g) were added to dried and freshly distilled tert-butyl alcohol (186 mmol, 17.8 mL) under an argon atmosphere. The reaction mixture was stirred at 60C overnight and then poured into saturated aqueous solution of NaHCO3 (60 mL) and washed with CH2Cl2 (2x40 mL). The aqueous phase was acidified with conc. H2SO4 (pH = 1) and extracted with CH2Cl2 (3 x 50 mL). The combined organic phases were washed with brine (15 mL), dried over Na2SO4 and concentrated give 5-tert-butoxy-5-oxopentanoic acid (2.67 g, 46%) as a colourless oil; 1H NMR (CDCl3): delta = 1.45 (s, 3H), 1.92 (m, 2H), 2.31 (t, J = 7.5 Hz, 2H), 2.42 (t, J = 7.5 Hz, 2H).
27%	With dmap; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; In toluene; at 20℃; for 8.5h;	A mixture of glutaric anhydride (10 g, 87.6 mmol), N-hydroxysuccinimide (3 g, 2.1 mmol), 4-dimethylaminopyridine (1.07 g, 8.8 mmol), anhydrous tert-butanol (24 mL, 262 mmol), and triethylamine (3.6 mL, 25.8 mmol) in dry toluene was mixed at room temperature for 30 min, then boiled for 8 hours, and allowed to stand over night at room temperature. The mixture was diluted with ethyl acetate (250 mL), washed with a 10% solution of citric acid (3×100 mL), then with a saturated salt solution (2×50 mL), and dried over anhydrous sodium sulfate, and the solvent was removed under vacuum. The product was isolated by flash chromatography on silica gel with an elution mixture of ethyl acetate-hexane (1:1). The yield of ether (1) in the form of colorless oil was 4.5 g (27%), [M+H]+=187.49.

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1501 - 1510
[2]Tetrahedron,2015,vol. 71,p. 8871 - 8875
[3]Chemistry - A European Journal,2020
[4]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055
[5]Patent: US2017/183318,2017,A1 .Location in patent: Paragraph 0207; 0208
[6]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560
[7]Journal of Medicinal Chemistry,2019,vol. 62,p. 6597 - 6614

5
[ 63128-51-8 ]
[ 6638-79-5 ]
[ 192123-40-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 2h;	EXAMPLE 40; Weinreb amide S2[00250] Weinreb amide S2: Prepared by a modification of a literature method. The starting carboxylic acid Sl (4.4 g, 23.4 mmol) was dissolved in CH2Cl2 (100 mL). N,O- dimethylhydroxylamineetaCl (2.51 g, 25.7 mmol), 1-hydroxybenzotriazole hydrate (3.93 g, <n="53"/>25.7 mmol), diisopropylethylamine (9.0 mL, 51.7 mmol), and EDCetaC1 (4.93 g, 25.7 mmol) were added sequentially to the reaction mixture. The solution was allowed to stir at room temperature for 2 h and then concentrated under vacuum to remove most of the CH2CI2. The crude material was diluted with EtOAc (300 mL), and washed successively with 5% aqueous NaHSO4 (3x), 5% aqueous NaHCtheta3 (3x), and brine. The organic layer was dried over MgSO4, filtered and concentrated to afford 5.14 g (95% yield) of the product as a pale yellow oil which was used without further purification. TLC Rf = 0.44 (EtOAc/hexanes, v/v, 1:2). 1HNMR (300MHz, CDCl3) delta 3.68 (s, 3H), 3.18 (s, 3H), 2.48 (t, J= 7.4 Hz, 2H), 2.30 (t, J = 7.4 Hz, 2H), 1.92 (m, 2H), 1.45 (s, 9H), FIG. 57. 13CNMR (75 MHz, CDCl3) delta 174.0, 172.7, 80.2, 77.5, 61.3, 35.0, 32.3, 31.0, 28.2, 20.2, FIG. 58. ESI-TOF-MS: [M+H]+ calculated 232.2, found 232.4.

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055
[2]Patent: WO2007/112358,2007,A1 .Location in patent: Page/Page column 51-52
[3]Journal of the Chemical Society. Perkin transactions I,1997,p. 1501 - 1510
[4]Journal of the Chemical Society. Perkin transactions I,1997,p. 1501 - 1510

6
[ 63128-51-8 ]
[ 126-81-8 ]
[ 208648-73-1 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 2189 - 2192
[2]Tetrahedron Letters,1998,vol. 39,p. 3585 - 3588

9
[ 43052-39-7 ]
alkali [ No CAS ]
aqueous dioxane [ No CAS ]
[ 63128-51-8 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1944,vol. 63,p. 189

10
di-tert-butyl glutarate [ No CAS ]
[ 63128-51-8 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1939,vol. 58,p. 1058

11
[ 63128-51-8 ]
[ 191090-32-1 ]
[ 637337-54-3 ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

12
[ 41355-50-4 ]
[ 63128-51-8 ]
[ 902760-42-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 4775 - 4780

13
[ 53715-97-2 ]
[ 75-65-0 ]
[ 63128-51-8 ]

Yield	Reaction Conditions	Operation in experiment
27%	With dmap; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; In toluene; at 115℃; for 16h;	EXAMPLE 39; Carboxylic acid SlO O>k O ^ ^ OH S1[00248] Carboxylic acid Sl: Prepared as previously described in the literature. Glutaric anhydride (10.0 g, 87.6 mmol) was weighed into a dry flask and purged with N2. Dry toluene (50 mL) was added followed by N-hydroxysuccinimide (3.0 g, 26.1 mmol), 4- dimethylaminopyridine (1.07 g, 8.8 mmol), anhydrous tert-butanol (24.3 mL, 262.3 mmol), and triethylamine (3.6 ml, 25.8 mmol). The flask was fitted with a reflux condenser, heated to 115C, and allowed to stir for 16 h under N2. The solution was cooled to room temperature, diluted with 300 mL EtOAc, and washed with 5% aqueous NaHSO4 (3x) followed by brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude material was purified by chromatography eluting with 1: 1 hexanes/EtOAc to yield 4.48 g (27% yield) of the product as a colorless oil. TLC Rf = 0.34 (EtOAc/hexanes, v/v, 1 : 1). 1HNMR (300MHz, CDCl3): delta 10.83 (br s, IH), 2.42 (t, J= 7.4 Hz, 2H), 2.31 (t, J= 2.31 Hz, 2H), 1.92 (m, 2H), 1.45 (s, 9H). FIG. 55. 13CNMR (75 MHz, CDCl3): delta 179.2, 172.3, 80.5, 34.4, 33.0, 28.0, 20.0. FIG. 56. ESI-TOF-MS: [M-H]" calculated 187.1, found 187.4.

Reference： [1]Patent: WO2007/112358,2007,A1 .Location in patent: Page/Page column 51

14
[ 63128-51-8 ]
C₂₅H₃₃NO₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055

15
[ 63128-51-8 ]
[ 941292-97-3 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055

16
[ 63128-51-8 ]
(R)-β-carboxyethyl-tert-butyl ester-γ-(S)-N-benzyl-α-methylbenzyl amino-propylalcohol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055

17
[ 63128-51-8 ]
C₁₀H₂₁NO₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055

18
[ 63128-51-8 ]
[ 941292-98-4 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055

19
[ 63128-51-8 ]
[ 192123-41-4 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055
[2]Journal of the Chemical Society. Perkin transactions I,1997,p. 1501 - 1510
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 6597 - 6614

20
[ 63128-51-8 ]
(S)-2-[(9H-fluoren-9-ylmethoxycarbonyl)aminomethyl]-pentanedioic acid 5-tert-butyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6050 - 6055
[2]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

21
[ 63128-51-8 ]
[ 637337-13-4 ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

22
[ 63128-51-8 ]
2-aminomethyl-pentanedioic acid 5-tert-butyl ester [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

23
[ 63128-51-8 ]
[ 637337-69-0 ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

24
[ 63128-51-8 ]
(S)-2-(Benzyloxycarbonylamino-methyl)-pentanedioic acid 1-benzyl ester [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

25
[ 63128-51-8 ]
H-(S)β²hGln(Trt)-OH [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

26
[ 63128-51-8 ]
[ 756531-84-7 ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

27
[ 63128-51-8 ]
[ 756531-82-5 ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

28
[ 63128-51-8 ]
[ 756531-77-8 ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

29
[ 63128-51-8 ]
[ 756531-78-9 ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

30
[ 63128-51-8 ]
[ 756531-86-9 ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

31
[ 63128-51-8 ]
2-[(9H-fluoren-9-ylmethoxycarbonylamino)-methyl]-4-(trityl-carbamoyl)-butyric acid [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 1545 - 1560

32
[ 63128-51-8 ]
[ 208648-74-2 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 2189 - 2192

33
[ 63128-51-8 ]
[ 338958-01-3 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 2189 - 2192

34
[ 63128-51-8 ]
2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoic acid 4-[4-carboxy-1-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-butylamino]-benzyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 2189 - 2192

35
[ 63128-51-8 ]
tert-butyl 5-(4-(N-9-fluorenylmethoxycarbonylleucinyl-oxymethyl)anilino)-5-(4,4-dimethylcyclohexylidene-2,6-dioxo)pentanoate [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 2189 - 2192

36
[ 63128-51-8 ]
5-(4,4-Dimethyl-2,6-dioxo-cyclohexylidene)-5-propylamino-pentanoic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 3585 - 3588

37
[ 63128-51-8 ]
5-(4,4-Dimethyl-2,6-dioxo-cyclohexylidene)-5-propylamino-pentanoic acid tert-butyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 3585 - 3588

38
[ 63128-51-8 ]
[ 733723-03-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1501 - 1510

39
[ 63128-51-8 ]
N-[4-(tert-Butoxycarbonyl)butyl]methionine [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1501 - 1510

40
[ 63128-51-8 ]
(S)-2-[(4-tert-Butoxycarbonyl-butyl)-trimethylsilanyl-amino]-3-methyl-pentanoic acid [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1501 - 1510

41
[ 59378-98-2 ]
[ 63128-51-8 ]

Yield	Reaction Conditions	Operation in experiment
15%		65.7 g (325 mmol) 2-c in 200 ml methanol were treated with 235 ml (970 mmol) 10% LiOH solution and stirred under ice cooling for 4 h. Using 2N HCl the reaction mixture was neutralized to a pH of 6.8. Methanol was distilled off and the aqueous residue was diluted with dichloromethane. At 0 C. the pH was brought to 3.8 with 10% citric acid. Standard work up yielded 8.9 g (15%) 2-d. ES-(-)MS (M-H)-187

Reference： [1]Patent: US2006/100158,2006,A1 .Location in patent: Page/Page column 31

42
C₁₂H₂₄N₂O₃ [ No CAS ]
[ 63128-51-8 ]
C₂₁H₃₈N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 1-[bis(dimethylamino)methylen]-1-H-benzotriazolim-tetrafluoroborate-3-oxide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃;	16.0 g (57.0 mmol) 2-b, 10.8 g (57.2 mmol) 2-d were dissolved in 320 ml THF, 14.9 ml (115.0 mmol) DIPEA, 18.6 g (58.0 mmol) TBTU and 7.7 g (57.0 mmol) HOBt were added and the mixture was stirred at room temperature over night. The mixture was evaporated and extracted with ethylacetate and saturated bicarbonate solution. The combined organic phases were concentrated. The residue was purified by MPLC (silica gel, cyclohexane/ethylacetate=7:3) to yield 14.2 g (60%) of 2-e. ES-MS (M+H)+415

Reference： [1]Patent: US2006/100158,2006,A1 .Location in patent: Page/Page column 31

43
C₅₃H₆₀N₃O₇Pol [ No CAS ]
[ 63128-51-8 ]
C₄₇H₆₄N₃O₈Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The synthesis of example 21 involves the preparation of a protected peptide fragment on solid phase and afterwards an acylation at the C-terminus in solution phase (see scheme B) The protected peptide fragment was synthesized by solid phase synthesis on a commercially available chlorotrityl-polystyrene resin (TCP resin, PepChem NMI TT GmbH)(10 g, 14 mmol). The first amino acid Fmoc-Statine (5.7 g, 28 mmol) was dissolved in dichloromethane (50 ml) and Dipea (15 ml) and was added to the resin. The suspension was shaken for 2 hours and methanol (20 ml) was added. After additional 20 minutes of agitation the resin was filtered and washed with dichloromethane (10×) and DMF (5×). Fmoc deprotections were performed by treatment of the resin with 30% piperidine in DMF for 2 and 20 minutes followed by washing the resin with DMF (10×). The acylation reactions were effected by treatment of the resin with a solution of TBTU (4 equiv.), HOBT (4 equiv.), Dipea (12 equiv.) and the corresponding Fmoc-amino acid or carboxylic acid (4 equiv.) in DMF at a concentration of 0.5 mol/l. In case of example 21 Fmoc-Nva, Fmoc-Ile and glutaric acid mono-tert.-butylester were coupled according to the peptide sequence. After completion of the peptide assembly the resin was treated with a solution of 30% hexafluoroisopropanol in dichloromethane (50 ml) for 3 hours. The resin was filtered, washed with dichloromethane and the filtrate was evaporated under reduced pressure. The crude product was purified by preparative reversed phase HPLC. The coupling of the protected peptide fragment (44.6 mg; 0.08 mmol) with amines (1.1 equiv., 0.088 mmol) was performed with TBTU (1.1 equiv., 0.088 mmol) in DMF with Dipea (2.5 equiv.) as base for 4 hours. In case of example 21 benzyl amine was applied. The solution was evaporated under reduced pressure, dissolved in methanol and again evaporated. The deprotection of the tBu-ester was performed with 90% TFA/water (2 ml) within 2 hours. The solution was evaporated and the residue was treated with saturated aq. LiOH solution (1 ml) and methanol (1 ml) for 1 hour. 95% TFA/water (300 mul) was added and the solution was evaporated under reduced pressure. The crude product was purified by preparative reversed phase HPLC applying an acetonitrile/water gradient. The product gave satisfactory analytical data. ES-MS: m/z=591.8 ([M+H]+)

Reference： [1]Patent: US2006/100158,2006,A1 .Location in patent: Page/Page column 43-44

44
[ 53715-97-2 ]
[ 63128-51-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran; water; ethyl acetate;	EXAMPLE 31 1-[N-(3-tert-Butoxycarbonylpropyl)carbamoyl]-5-fluorouracil Glutaric anhydride (11.41 g.) was added portion-wise to a solution of potassium tert-butoxide (14.02 g.) in tetrahydrofuran (100 ml.) at ambient temperature. After the exothermic reaction was ceased, the reaction mixture was stirred at 40 C. for 15 minutes. Tetrahydrofuran was distilled off under reduced pressure. The residue was dissolved in water. After ethyl acetate was added, the solution was adjusted to pH 9 with aqueous potassium carbonate solution under ice-cooling. The separated water layer was washed with ethyl acetate, treated with activated charcoal, overlapped with ethyl acetate, and then adjusted to pH 4.0 with 10% hydrochloric acid under ice-cooling. The ethyl acetate layer was dried over magnesium sulfate, treated with activated charcoal, filtered and concentrated under reduced pressure to give glutaric acid mono-tert-butyl ester (10 g.).

Reference： [1]Patent: US4349552,1982,A

Yield	Reaction Conditions	Operation in experiment
40%		EXAMPLE 13 Synthesis of Mono-t-butyl Glutarate Glutaric acid anhydride (5.0 g, 44 mmol) and dimethylaminopyridine (5.4 g, 44 mmol) were dissolved in 70 ml of dichloromethane. To this, under cooling at 0 C., was added t-butyl alcohol (3.3 g, 44 mmol). Being intact, stirring continued at room temperature overnight, and then, a majority of methylene chloride was recovered and 100 ml of water was added. The aqueous phase was acidified with citric acid and extracted with ethyl acetate. After the organic phase was washed with saturated brine and dried over anhydrous sodium sulfate, solvent was removed to afford 3.3 g of the t-butyl ester (yield: 40%).

Yield	Reaction Conditions	Operation in experiment
75%		A 1M aqueous solution of lithium hydroxide (12.72 ml, 12.72 mmol) was added to a solution of diester (A8) (2.57 g, 12.72 mmol) in dioxane (20 ml) at 0 C. The solution was allowed to warm to ambient temperature and stirred for sixteen hours. The solution was concentrated under reduced pressure and aqueous saturated sodium hydrogen carbonate (20 ml) was added. The resultant solution was extracted with ethyl acetate (210 ml). The combined organic extracts were washed with aqueous saturated sodium hydrogen carbonate (10 ml). The aqueous extracts were combined and acidified to pH 4 with 10% aqueous citric acid. The acidified solution was extracted with ethyl acetate (520 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent was removed under reduced pressure to afford mono-tert-butylglutarate acid (A9) as a clear liquid (1.80 g, 75%), RF 0.6 (Ethyl acetate, KMnO4).

47
[ 63128-51-8 ]
C₁₉H₃₀N₂O₉S [ No CAS ]
[ 1048667-36-2 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 2973 - 2982

48
[ 63128-51-8 ]
C₁₉H₃₀N₂O₉S [ No CAS ]
[ 1048667-37-3 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 2973 - 2982

49
[ 63128-51-8 ]
[ 76197-90-5 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 385 - 386

50
[ 75-91-2 ]
[ 504-02-9 ]
[ 110-94-1 ]
[ 3885-29-8 ]
[ 868-57-5 ]
[ 63128-51-8 ]
[ 75-07-0 ]
[ 141-78-6 ]
[ 75-65-0 ]

Reference： [1]Russian Journal of General Chemistry,2011,vol. 81,p. 550 - 558

51
[ 63128-51-8 ]
[ 1408065-79-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 8216 - 8235

52
[ 63128-51-8 ]
[ 1408065-29-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 8216 - 8235

53
[ 63128-51-8 ]
[ 1408065-31-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 8216 - 8235

54
[ 63128-51-8 ]
[ 1408065-33-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 8216 - 8235

55
[ 63128-51-8 ]
[ 131230-76-7 ]
[ 1408065-78-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 8216 - 8235

56
[ 63128-51-8 ]
[ 1538554-90-3 ]
[ 1538554-91-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	With chloro-N,N,N',N'-bis(tetramethylene)formamidinium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 15h;	Step B - Synthesis of Intermediate Compound Int-lic: To a solution of compound Tnt-lla (380 mg, 1.1 mmol) in DMF (10.0 mL) was added <strong>[63128-51-8]5-tert-butoxy-5-oxopentanoic acid</strong> (Int-llb) (210 mg, 1.1 mmol), DIPEA (200 mg, 1.6 mmol) and PyClu (480 mg, 1.5 mmol). After stirring at room temperature for about 15 hours, the mixture was concentrated in vacuo and the resulting residue was dissolved indichloromethane (50.0 mL). The solution was washed with a 1.0 M HC1 solution and brine and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residueobtained was purified using prep-TLC (50/1 dichloromethane/MeOH) to provide compound(310 mg, 53%). ?HNMR (400 MHz, CDC13) 5.83-5.85 (d, J= 8.0 Hz, 1H), 5.18-5.231H), 3.95 (s, 3H), 3.54-3.60 (m, 1H), 3.51 (s, 3H), 3.12 (s, 3H), 2.44-2.48 (m, 2H), 2.28-2.322H), 2.08-2.13 (m, 2H), 1.83-1.95 (m, 4H)., 1.49 (s, 9H), 1.12-1.21 (m, 2H). LCMS anal. calcd. for C22H33N309S: 515.1; Found: 538.1 (M+Na)
53%	With chloro-N,N,N',N'-bis(tetramethylene)formamidinium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 15h;	Step B - Synthesis of Intermediate Compound Int-llc To a solution of compound Int-lla (380 mg, 1.1 mmol) in DMF (10.0 mL) was added <strong>[63128-51-8]5-tert-butoxy-5-oxopentanoic acid</strong> (Int-llb) (210 mg, 1.1 mmol), DIPEA (200 mg, 1.6 mmol) and PyClu (480 mg, 1.5 mmol). After stirring at room temperature for about 15 hours, the mixture was concentrated in vacuo and the resulting residue was dissolved in dichloromethane (50.0 mL). The solution was washed with a 1.0 M HCl solution and brine and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue obtained was purified using prep-TLC (50/1 dichloromethane/MeOH) to provide compound Int- 11c (310 mg, 53%). 1H NMR (400 MHz, CDC13) delta 5.83-5.85 (d, J= 8.0 Hz, 1H), 5.18-5.23 (m, 1H), 3.95 (s, 3H), 3.54-3.60 (m, 1H), 3.51 (s, 3H), 3.12 (s, 3H), 2.44-2.48 (m, 2H), 2.28-2.32 (m, 2H), 2.08-2.13 (m, 2H), 1.83-1.95 (m, 4H)., 1.49 (s, 9H), 1.12-1.21 (m, 2H). LCMS anal, calcd. for C22H33N309S: 515.1; Found: 538.1 (M+Na)+.
53%	With chloro-N,N,N',N'-bis(tetramethylene)formamidinium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 15h;	To a solution of compound Int-11a (380 mg, 1.1 mmol) in DMF (10.0 mL) was added <strong>[63128-51-8]5-tert-butoxy-5-oxopentanoic acid</strong> (Int-11b) (210 mg, 1.1 mmol), DIPEA (200 mg, 1.6 mmol) and PyClu (480 mg, 1.5 mmol). After stirring at room temperature for about 15 hours, the mixture was concentrated in vacuo and the resulting residue was dissolved in dichloromethane (50.0 mL). The solution was washed with a 1.0 M HCl solution and brine and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue obtained was purified using prep-TLC (50/1 dichloromethane/MeOH) to provide compound Int-11c (310 mg, 53%). 1H NMR (400 MHz, CDCl3) delta 5.83-5.85 (d, J=8.0 Hz, 1H), 5.18-5.23 (m, 1H), 3.95 (s, 3H), 3.54-3.60 (m, 1H), 3.51 (s, 3H), 3.12 (s, 3H), 2.44-2.48 (m, 2H), 2.28-2.32 (m, 2H), 2.08-2.13 (m, 2H), 1.83-1.95 (m, 4H), 1.49 (s, 9H), 1.12-1.21 (m, 2H). LCMS anal. calcd. for C22H33N3O9S: 515.1. Found: 538.1 (M+Na)+.

Reference： [1]Patent: WO2014/11769,2014,A1 .Location in patent: Page/Page column 47; 48
[2]Patent: WO2014/8636,2014,A1 .Location in patent: Page/Page column 47; 48
[3]Patent: US2015/203512,2015,A1 .Location in patent: Paragraph 0222; 0224

57
[ 63128-51-8 ]
[ 1538554-94-7 ]
[ 1538554-95-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 38℃; for 3h;	Step B - Synthesis of Intermediate Compound Int-6cTo a solution of compound Int-12b (400 mg, 0.70 mmol) and Pentanedioic acid mono-tert-butyl ester mt-lOb (263 mg, 1.40 mmol) in dichloromethane (5 mL) was added HATU (420 mg, 1.40 mmol) and DIEA (180 mg, 1.40 mmol). The mixture was allowed to stir for 3 hours at 38 C and then quenched by addition of aqueous NH4C1. The mixture was extracted with dichloromethane and the combined organic layer was dried over Na2SO4, filteredand concentrated in vacuo. The crude residue was purified using prep-TLC to provide the product Int-12c (400 mg, 93%). LCMS anal. calcd. for: C32H44FN508 645.1; Found: 646.2 (M+ 1 )

Reference： [1]Patent: WO2014/11769,2014,A1 .Location in patent: Page/Page column 49; 50
[2]Patent: US2015/203512,2015,A1 .Location in patent: Paragraph 0228; 0230

58
[ 63128-51-8 ]
C₂₃H₃₀FN₅O₅ [ No CAS ]
[ 1538554-95-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 38℃; for 3h;	Step B - Synthesis of Intermediate Compound Int-6c To a solution of compound Int-12b (400 mg, 0.70 mmol) and Pentanedioic acid mono-tert-butyl ester Int-lOb (263 mg, 1.40 mmol) in dichloromethane (5 mL) was added HATU (420 mg, 1.40 mmol) and DIEA (180 mg, 1.40 mmol). The mixture was allowed to stir for 3 hours at 38 C and then quenched by addition of aqueous H4C1. The mixture was extracted with dichloromethane and the combined organic layer was dried over Na2S04, filtered and concentrated in vacuo. The crude residue was purified using prep-TLC to provide the product Int-12c (400 mg, 93%). LCMS anal, calcd. for: C32H44FN508 645.1; Found: 646.2 (M+l)+.

Reference： [1]Patent: WO2014/8636,2014,A1 .Location in patent: Page/Page column 49; 50

59
[ 63128-51-8 ]
[ 74-88-4 ]
[ 59378-98-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In acetone; for 17h;Reflux;	5-tert-Butoxy-5-oxopentanoic acid (0.95 mmol, 0.18 g) was dissolved in dry acetone (3 mL) and K2CO3 (3.79 mmol, 0.52 g) and MeI (9.47 mmol, 0.59 mL) were added. The reaction mixture was refluxed for 17 h, then was allowed to cool down and was quenched with ethyl acetate (20 mL). The mixture was washed with brine (2 x 10 mL), dried over Na2SO4 and concentrated to give tert-butyl methyl glutarate 1j (0.17 g, 91%) as a slightly yellow oil; 1H NMR (CDCl3): delta = 1.44 (s, 9H), 1.91 (m, 2H), 2.28 (t, J = 7.2 Hz, 2H), 2.37 (t, J = 7.5 Hz, 2H), 3.68 (s, 3H); 13C NMR (CDCl3): delta = 20.3, 28.1, 33.1, 34.5, 51.5,80.3, 172.2, 173.5.

Reference： [1]Tetrahedron,2015,vol. 71,p. 8871 - 8875

60
[ 63128-51-8 ]
[ 87517-46-2 ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 8871 - 8875

61
[ 63128-51-8 ]
(E)-8-tert-butoxy-4,8-dioxooct-2-enoic acid [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 8871 - 8875

62
[ 63128-51-8 ]
(2S,3R,4S,5S,6S)-2-(((S)-6-(5-(tert-butoxy)-5-oxopentanoyl)-8-(chloromethyl)-1-methyl-7,8-dihydro-6H-thieno[3,2-e]indol-4-yl)oxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]

Reference： [1]Patent: US2016/271270,2016,A1

63
[ 63128-51-8 ]
tert-butyl 5-chloro-5-oxopentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; at 0℃; for 0.5h;	Step 1: Synthesis of tert-butyl 5-chloro-5-oxopentanoate (44): To a solution of <strong>[63128-51-8]5-(tert-butoxy)-5-oxopentanoic acid</strong> (110 mg, 0.58 mmol) in THF (3 mL), was added oxalyl chloride (0.58 mL, 1.2 mmol, 2M in DCM) at 0 C., followed by 1 drop of DMF. The mixture was stirred at 0 C. for 30 min, and concentrated in vacuo to give the corresponding acid chloride 44 as white solid.

Reference： [1]Patent: US2016/271270,2016,A1 .Location in patent: Paragraph 0325; 0326
[2]Chemistry - A European Journal,2020

64
[ 63128-51-8 ]
tert-butyl (S)-5-(4-(benzyloxy)-8-(chloromethyl)-1-methyl-7,8-dihydro-6H-thieno[3,2-e]indol-6-yl)-5-oxopentanoate [ No CAS ]

Reference： [1]Patent: US2016/271270,2016,A1

65
[ 63128-51-8 ]
C₂₄H₂₃Cl₂NO₃S [ No CAS ]

Reference： [1]Patent: US2016/271270,2016,A1

66
[ 63128-51-8 ]
(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((S)-8-(chloromethyl)-1-methyl-7,8-dihydro-6H-thieno[3,2-e]indol-4-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]
(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((S)-6-(5-(tert-butoxy)-5-oxopentanoyl)-8-(chloromethyl)-1-methyl-7,8-dihydro-6H-thieno[3,2-e]indol-4-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		A solution of <strong>[63128-51-8]5-(tert-butoxy)-5-oxopentanoic acid</strong> (44, 191 mg, 1.02 mmol,) in THF (10 mL) was cooled to 0 C. and oxalyl chloride (1.02 mL, 2M in DCM) was added followed by 1 drop of DMF. The mixture was stirred at 0 C. for 30 min, and concentrated in vacuum to give the corresponding acid chloride as wax. This was dissolved in THF (10 mL), and added to a solution of 79 (526 mg, 0.85 mmol) in THF (10 mL), and followed by Et3N (0.354 mL, 2.54 mmol).

Reference： [1]Patent: US2016/271270,2016,A1 .Location in patent: Paragraph 0366; 0371

67
[ 63128-51-8 ]
[ 55-36-7 ]
C₁₄H₂₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		1,1?-carbonyldiimidazole (2.26 g, 14 mmol) was added to a solution of monoether (1) (2.2 g, 11.7 mmol) in 50 mL of anhydrous tetrahydrofuran, and the mixture was boiled for 1 hour. Then, the mixture was cooled to room temperature, and histamine gihydrochloride (2.15 g, 11.7 mmol) and triethylamine (3.28 mL, 23.4 mmol) were added thereto. The reaction mass was stirred for 8 hours at room temperature, poured into 100 mL of a 10% potash solution, extracted with dicloromethane (3×75 mL), dried over anhydrous sodium sulfate, and the solvent was removed under vacuum. The target product was isolated by flash chromatography on silica gel, with an elution mixture of dichloromethane-methanol (10:1). After recrystallization, the yield of the target product in the form of white crystals was 1.1 g (33%). LC/MS, an individual peak at a retention time of 0.93, min [M+H]+=282 (condition G). HPLC under condition 6, individual peak at a retention time of 13.4 min. 1H NMR (400.13 MHz, DMSO-d6, delta, m.d., J/Hz): 1.38 (s, 9H, CH3CH), 1.68 (quin, 2H, CH2CH2CH2, J=7.5 Hz); 2.06 (t, 2H, CH2CONH, J=7.4 Hz); 2.15 (t, 2H, CH2COO, J=7.4 Hz); 2.60 (t, 2H, CH2C, J=7.4 Hz); 3.24 (m, 2H, CH2N); 6.73 (br s, 1H, CCH); 7.46 (d, 1H, NCHN, J=1 Hz); 7.70 (br s, 1H, NH); 11.67 (br s, 1H, NH).

Reference： [1]Patent: US2017/183318,2017,A1 .Location in patent: Paragraph 0207; 0209

68
[ 63128-51-8 ]
[ 105047-45-8 ]
N6-(5-(tert-butoxy)-5-oxopentanoyl)-N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-L-lysine [ No CAS ]