(S)-1-{(S)-2-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyryl}-pyrrolidine-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-1-{(S)-2-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyryl}-pyrrolidine-2-carboxylic acid tert-butyl ester
• CAS No.: 205498-74-4
• Molecular Formula: C₂₈H₄₃N₃O₆
• Molecular Weight: 517.666

Synonyms:(S)-1-{(S)-2-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyryl}-pyrrolidine-2-carboxylic acid tert-butyl ester

Chemical Property of (S)-1-{(S)-2-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyryl}-pyrrolidine-2-carboxylic acid tert-butyl ester

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Technology Process of (S)-1-{(S)-2-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyryl}-pyrrolidine-2-carboxylic acid tert-butyl ester

There total 4 articles about (S)-1-{(S)-2-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyryl}-pyrrolidine-2-carboxylic 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: 93.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + (S)-1-((S)-3-Methyl-2-methylamino-butyryl)-pyrrolidine-2-carboxylic acid tert-butyl ester; hydrochloride → (S)-1-{(S)-2-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyryl}-pyrrolidine-2-carboxylic acid tert-butyl ester (205498-74-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jm970800t

Reference yield:

Z-MeVal-OH (42417-65-2) → (S)-1-{(S)-2-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyryl}-pyrrolidine-2-carboxylic acid tert-butyl ester (205498-74-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / diisopropylethylamine, tripyrrolidinobromophosphonium hexafluorophosphate / CH₂Cl₂ / 1 h / Ambient temperature

2: 99 percent / H₂, 12N HCl / 10percent Pd/C / methanol / 16 h / 760 Torr / Ambient temperature

3: 93 percent / diisopropylethylamine, tripyrrolidinobromophosphonium hexafluorophosphate / CH₂Cl₂ / 1 h / Ambient temperature

With hydrogenchloride; hydrogen; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jm970800t

Reference yield:

proline tert-butyl ester (2812-46-6) → (S)-1-{(S)-2-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyryl}-pyrrolidine-2-carboxylic acid tert-butyl ester (205498-74-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / diisopropylethylamine, tripyrrolidinobromophosphonium hexafluorophosphate / CH₂Cl₂ / 1 h / Ambient temperature

2: 99 percent / H₂, 12N HCl / 10percent Pd/C / methanol / 16 h / 760 Torr / Ambient temperature

3: 93 percent / diisopropylethylamine, tripyrrolidinobromophosphonium hexafluorophosphate / CH₂Cl₂ / 1 h / Ambient temperature

With hydrogenchloride; hydrogen; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jm970800t

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

Z-MeVal-OH

proline tert-butyl ester

(S)-1-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Downstream raw materials:

(2R,3R)-3-Methoxy-2-methyl-N-((S)-2-phenyl-1-thiazol-2-yl-ethyl)-3-[(S)-1-((S)-pyrrolidine-2-carbonyl)-pyrrolidin-2-yl]-propionamide

(S)-1-((S)-2-{[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carboxylic acid

(S)-1-((S)-2-{[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carboxylic acid tert-butyl ester

[(S)-1-((S)-2-{(S)-2-[(1R,2R)-1-Methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester

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