(S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester
• CAS No.: 87113-91-5
• Molecular Formula: C₂₄H₃₁NO₃
• Molecular Weight: 381.515
• Mol file: 87113-91-5.mol

Synonyms:(S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property of (S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of (S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester

There total 2 articles about (S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl 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: 100.0%

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) + (adamant-1-yl)-acetic acid (4942-47-6) → (S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester (87113-91-5)

Guidance literature:

With N-Ethylmaleimide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1021/jm00369a017

Reference yield: 48.0%

(adamant-1-yl)-acetic acid (4942-47-6) + H-Pro-OBzl (41324-66-7) → (S)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-isobutyl ester (96847-85-7) + (S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester (87113-91-5)

Guidance literature:

In acetonitrile; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2007.06.019

Reference yield:

(S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester (87113-91-5) → N-(1-adamantylacetyl)-L-prolyl-DL-α-methylphenylalanyl-Nω-nitro-L-arginine methyl ester (87113-93-7)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / ethanol / 3102.9 Torr

2: 88 percent / HOBt, NEM, DCC / tetrahydrofuran / pH 7.0-7.5

With N-Ethylmaleimide; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1021/jm00369a017

upstream raw materials:

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

(adamant-1-yl)-acetic acid

H-Pro-OBzl

Downstream raw materials:

N-(1-adamantylacetyl)-L-prolyl-DL-α-methylphenylalanyl-L-arginine

N-(1-adamantylacetyl)-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-L-arginine

N-(1-adamantylacetyl)-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-L-arginine methyl ester