(S)-1-{(S)-4-[(Benzhydryl-carbamoyl)-methoxycarbonyl]-4-tert-butoxycarbonylamino-butyryl}-pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (S)-1-{(S)-4-[(Benzhydryl-carbamoyl)-methoxycarbonyl]-4-tert-butoxycarbonylamino-butyryl}-pyrrolidine-2-carboxylic acid
• CAS No.: 200399-55-9
• Molecular Formula: C₃₀H₃₇N₃O₈
• Molecular Weight: 567.639
• Mol file: 200399-55-9.mol

Synonyms:(S)-1-{(S)-4-[(Benzhydryl-carbamoyl)-methoxycarbonyl]-4-tert-butoxycarbonylamino-butyryl}-pyrrolidine-2-carboxylic acid

Chemical Property of (S)-1-{(S)-4-[(Benzhydryl-carbamoyl)-methoxycarbonyl]-4-tert-butoxycarbonylamino-butyryl}-pyrrolidine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-{(S)-4-[(Benzhydryl-carbamoyl)-methoxycarbonyl]-4-tert-butoxycarbonylamino-butyryl}-pyrrolidine-2-carboxylic acid

There total 5 articles about (S)-1-{(S)-4-[(Benzhydryl-carbamoyl)-methoxycarbonyl]-4-tert-butoxycarbonylamino-butyryl}-pyrrolidine-2-carboxylic acid 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: 73.3%

(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] ester 5-(2,5-dioxo-pyrrolidin-1-yl) ester + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (S)-1-{(S)-4-[(Benzhydryl-carbamoyl)-methoxycarbonyl]-4-tert-butoxycarbonylamino-butyryl}-pyrrolidine-2-carboxylic acid (200399-55-9)

Guidance literature:

With 15-crown-5; sodium methylate; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0968-0896(97)00141-7

Reference yield:

Boc-Glu (2419-94-5) → (S)-1-{(S)-4-[(Benzhydryl-carbamoyl)-methoxycarbonyl]-4-tert-butoxycarbonylamino-butyryl}-pyrrolidine-2-carboxylic acid (200399-55-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / CH₃ONa, 15-crown-5 / ethyl acetate / 3 h / 50 °C

2: DCC / tetrahydrofuran / Ambient temperature

3: 73.3 percent / MeONa, 15-crown-5 / dimethylformamide / Ambient temperature

With 15-crown-5; sodium methylate; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00141-7

Reference yield:

N-benzhydryl-2-bromoacetamide (119706-03-5) → (S)-1-{(S)-4-[(Benzhydryl-carbamoyl)-methoxycarbonyl]-4-tert-butoxycarbonylamino-butyryl}-pyrrolidine-2-carboxylic acid (200399-55-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / CH₃ONa, 15-crown-5 / ethyl acetate / 3 h / 50 °C

2: DCC / tetrahydrofuran / Ambient temperature

3: 73.3 percent / MeONa, 15-crown-5 / dimethylformamide / Ambient temperature

With 15-crown-5; sodium methylate; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00141-7

upstream raw materials:

L-proline

Boc-Glu

N-benzhydryl-2-bromoacetamide

(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] ester

Downstream raw materials:

(7S,9aS)-4,9-Dioxo-decahydro-3a,8-diaza-cyclopentacyclooctene-7-carboxylic acid (benzhydryl-carbamoyl)-methyl ester