(S)-2-((S)-2-{(S)-2-[(S)-2-(Benzyloxycarbonylmethyl-carbamoyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-((S)-2-{(S)-2-[(S)-2-(Benzyloxycarbonylmethyl-carbamoyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 87215-52-9
• Molecular Formula: C₃₄H₄₇N₅O₈
• Molecular Weight: 653.776

Synonyms:(S)-2-((S)-2-{(S)-2-[(S)-2-(Benzyloxycarbonylmethyl-carbamoyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (S)-2-((S)-2-{(S)-2-[(S)-2-(Benzyloxycarbonylmethyl-carbamoyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (S)-2-((S)-2-{(S)-2-[(S)-2-(Benzyloxycarbonylmethyl-carbamoyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 4 articles about (S)-2-((S)-2-{(S)-2-[(S)-2-(Benzyloxycarbonylmethyl-carbamoyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-pyrrolidine-1-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: 68.0%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + H-(Pro)3-Gly-OBzl*HCl → (S)-2-((S)-2-{(S)-2-[(S)-2-(Benzyloxycarbonylmethyl-carbamoyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (87215-52-9)

Guidance literature:

With TEA; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; 1.) 0 degC, 1h, 2.) room temperature, overnight;

DOI:10.1246/bcsj.57.1679

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → (S)-2-((S)-2-{(S)-2-[(S)-2-(Benzyloxycarbonylmethyl-carbamoyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (87215-52-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / TEA, EDC*HCl / CHCl₃ / 1.) 0 degC, 1h, 2.) room temperature, overnight

2: HCl / formic acid / 0.5 h / Ambient temperature

3: 68 percent / TEA, EDC*HCl / CHCl₃ / 1.) 0 degC, 1h, 2.) room temperature, overnight

With hydrogenchloride; TEA; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In formic acid; chloroform;

DOI:10.1246/bcsj.57.1679

Reference yield:

H-(Pro)2-Gly-OBzl*HCl → (S)-2-((S)-2-{(S)-2-[(S)-2-(Benzyloxycarbonylmethyl-carbamoyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (87215-52-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / TEA, EDC*HCl / CHCl₃ / 1.) 0 degC, 1h, 2.) room temperature, overnight

2: HCl / formic acid / 0.5 h / Ambient temperature

3: 68 percent / TEA, EDC*HCl / CHCl₃ / 1.) 0 degC, 1h, 2.) room temperature, overnight

With hydrogenchloride; TEA; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In formic acid; chloroform;

DOI:10.1246/bcsj.57.1679

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

Boc-(Pro)3-Gly-OBzl

Downstream raw materials:

{[(S)-1-((S)-1-{(S)-1-[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonyl}-pyrrolidine-2-carbonyl)-pyrrolidine-2-carbonyl]-amino}-acetic acid benzyl ester

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