[(R)-3-Benzyl-1-((S)-1-benzylcarbamoyl-5-benzyloxycarbonylamino-pentyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

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Chemical Name:[(R)-3-Benzyl-1-((S)-1-benzylcarbamoyl-5-benzyloxycarbonylamino-pentyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester
CAS No.:246870-34-8
Molecular Formula:C₃₇H₄₆N₄O₆
Molecular Weight:642.795
Hs Code.:

Synonyms:[(R)-3-Benzyl-1-((S)-1-benzylcarbamoyl-5-benzyloxycarbonylamino-pentyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

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Chemical Property of [(R)-3-Benzyl-1-((S)-1-benzylcarbamoyl-5-benzyloxycarbonylamino-pentyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

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Technology Process of [(R)-3-Benzyl-1-((S)-1-benzylcarbamoyl-5-benzyloxycarbonylamino-pentyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

There total 10 articles about [(R)-3-Benzyl-1-((S)-1-benzylcarbamoyl-5-benzyloxycarbonylamino-pentyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester 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: 86.0%

: [(R)-3-((S)-1-Benzylcarbamoyl-5-benzyloxycarbonylamino-pentylcarbamoyl)-3-tert-butoxycarbonylamino-4-phenyl-butyl]-dimethyl-sulfonium; iodide

: 246870-34-8
[(R)-3-Benzyl-1-((S)-1-benzylcarbamoyl-5-benzyloxycarbonylamino-pentyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Guidance literature:: With sodium hydride; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 2h;
DOI:10.1016/S0040-4020(99)00561-X

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 246870-34-8
[(R)-3-Benzyl-1-((S)-1-benzylcarbamoyl-5-benzyloxycarbonylamino-pentyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / Et₃N / tetrahydrofuran / 6 h / 20 °C

2: 82 percent / aq. NaOH / dioxane / 5 h / Heating

3: 37 percent / HOBT; EDCI / CH₂Cl₂ / 20 °C

4: 100 percent / 20 h / 20 °C

5: 86 percent / NaH / dimethylformamide; CH₂Cl₂ / 2 h / 0 °C

With sodium hydroxide; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Hydrolysis / 3: Condensation / 4: Alkylation / 5: Cyclization;
DOI:10.1016/S0040-4020(99)00561-X

Reference yield:

: 2389-45-9
Boc-Lys(Z)-OH

: 246870-34-8
[(R)-3-Benzyl-1-((S)-1-benzylcarbamoyl-5-benzyloxycarbonylamino-pentyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: HOBT; EDCI / 12 h / 20 °C

1.2: 66 percent / CF₃COOH / CHCl₃ / 12 h / 20 °C

2.1: 37 percent / HOBT; EDCI / CH₂Cl₂ / 20 °C

3.1: 100 percent / 20 h / 20 °C

4.1: 86 percent / NaH / dimethylformamide; CH₂Cl₂ / 2 h / 0 °C

With sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; 1.1: Condensation / 1.2: Hydrolysis / 2.1: Condensation / 3.1: Alkylation / 4.1: Cyclization;
DOI:10.1016/S0040-4020(99)00561-X