(4S)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-5-hydroxy-6-(4-phenyl-butyrylamino)hexanamide

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Chemical Name:(4S)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-5-hydroxy-6-(4-phenyl-butyrylamino)hexanamide
CAS No.:387338-08-1
Molecular Formula:C₂₃H₃₇N₃O₅
Molecular Weight:435.564
Hs Code.:

Synonyms:(4S)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-5-hydroxy-6-(4-phenyl-butyrylamino)hexanamide

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Chemical Property of (4S)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-5-hydroxy-6-(4-phenyl-butyrylamino)hexanamide

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Technology Process of (4S)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-5-hydroxy-6-(4-phenyl-butyrylamino)hexanamide

There total 7 articles about (4S)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-5-hydroxy-6-(4-phenyl-butyrylamino)hexanamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

: 1821-12-1
4-Phenylbutyric acid

: [3-amino-1-(2-dimethylcarbamoyl-ethyl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester; compound with acetic acid

: 387338-08-1
(4S)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-5-hydroxy-6-(4-phenyl-butyrylamino)hexanamide

Guidance literature:: 4-Phenylbutyric acid; With chloroformic acid ethyl ester; triethylamine; In dichloromethane; at 0 ℃; for 0.333333h;

[3-amino-1-(2-dimethylcarbamoyl-ethyl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester; compound with acetic acid; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Further stages.;
DOI:10.1021/jo0157831

Reference yield:

: 72468-46-3
N²-(tert-butyloxycarbonyl)-N⁵,N⁵-dimethylglutamine benzyl ester

: 387338-08-1
(4S)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-5-hydroxy-6-(4-phenyl-butyrylamino)hexanamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / H₂ / 10percent Pd/C / methanol / 6 h

2.1: ClCOOEt₃; Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

2.2: 78 percent / DMAP / CH₂Cl₂ / 2 h / 0 °C

3.1: 91 percent / triethylsilane / 10percent Pd/C / dimethylformamide / 2 h / 0 °C

4.1: 70 percent / AcOH / methanol / 18 h / 20 °C

5.1: 43 percent / H₂ / PtO₂ / propan-2-ol / 24 h / 2585.81 Torr

6.1: ClCOOEt; Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

6.2: 61 percent / Et₃N / CH₂Cl₂ / 3 h / 0 - 20 °C

With triethylsilane; hydrogen; chloroformic acid ethyl ester; acetic acid; triethylamine; platinum(IV) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo0157831

Reference yield:

: 30924-93-7
Boc-Glu-OBn

: 387338-08-1
(4S)-N,N-dimethyl-4-(tert-butyloxycarbonylamino)-5-hydroxy-6-(4-phenyl-butyrylamino)hexanamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: ClCOOEt; Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

1.2: 85 percent / Et₃N / CH₂Cl₂

2.1: 90 percent / H₂ / 10percent Pd/C / methanol / 6 h

3.1: ClCOOEt₃; Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

3.2: 78 percent / DMAP / CH₂Cl₂ / 2 h / 0 °C

4.1: 91 percent / triethylsilane / 10percent Pd/C / dimethylformamide / 2 h / 0 °C

5.1: 70 percent / AcOH / methanol / 18 h / 20 °C

6.1: 43 percent / H₂ / PtO₂ / propan-2-ol / 24 h / 2585.81 Torr

7.1: ClCOOEt; Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

7.2: 61 percent / Et₃N / CH₂Cl₂ / 3 h / 0 - 20 °C

With triethylsilane; hydrogen; chloroformic acid ethyl ester; acetic acid; triethylamine; platinum(IV) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo0157831