3-{(R)-2-[((S)-1-Methoxyoxalyl-pyrrolidine-2-carbonyl)-amino]-3-phenyl-propionylamino}-propionic acid tert-butyl ester

Base Information

• Chemical Name: 3-{(R)-2-[((S)-1-Methoxyoxalyl-pyrrolidine-2-carbonyl)-amino]-3-phenyl-propionylamino}-propionic acid tert-butyl ester
• CAS No.: 207445-02-1
• Molecular Formula: C₂₄H₃₃N₃O₇
• Molecular Weight: 475.542

Synonyms:3-{(R)-2-[((S)-1-Methoxyoxalyl-pyrrolidine-2-carbonyl)-amino]-3-phenyl-propionylamino}-propionic acid tert-butyl ester

Chemical Property of 3-{(R)-2-[((S)-1-Methoxyoxalyl-pyrrolidine-2-carbonyl)-amino]-3-phenyl-propionylamino}-propionic acid tert-butyl ester

Chemical Property:

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Technology Process of 3-{(R)-2-[((S)-1-Methoxyoxalyl-pyrrolidine-2-carbonyl)-amino]-3-phenyl-propionylamino}-propionic acid tert-butyl ester

There total 5 articles about 3-{(R)-2-[((S)-1-Methoxyoxalyl-pyrrolidine-2-carbonyl)-amino]-3-phenyl-propionylamino}-propionic 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:

Cbz-D-Phe (2448-45-5) → 3-{(R)-2-[((S)-1-Methoxyoxalyl-pyrrolidine-2-carbonyl)-amino]-3-phenyl-propionylamino}-propionic acid tert-butyl ester (207445-02-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / water soluble carbodiimide hydrochloride, HOBt, DMAP, TEA / dimethylformamide / Ambient temperature

2: H₂ / Pd/C / methanol

3: water soluble carbodiimide hydrochloride, HOBt, DMAP, TEA / dimethylformamide / Ambient temperature

4: H₂ / Pd/C / methanol

5: Et₃N / CH₂Cl₂

With dmap; TEA; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.46.697

Reference yield:

3-((R)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-propionic acid tert-butyl ester (207445-00-9) → 3-{(R)-2-[((S)-1-Methoxyoxalyl-pyrrolidine-2-carbonyl)-amino]-3-phenyl-propionylamino}-propionic acid tert-butyl ester (207445-02-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd/C / methanol

2: water soluble carbodiimide hydrochloride, HOBt, DMAP, TEA / dimethylformamide / Ambient temperature

3: H₂ / Pd/C / methanol

4: Et₃N / CH₂Cl₂

With dmap; TEA; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.46.697

Reference yield:

tert-butyl 3-aminopropanoate hydrochloride (58620-93-2) → 3-{(R)-2-[((S)-1-Methoxyoxalyl-pyrrolidine-2-carbonyl)-amino]-3-phenyl-propionylamino}-propionic acid tert-butyl ester (207445-02-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / water soluble carbodiimide hydrochloride, HOBt, DMAP, TEA / dimethylformamide / Ambient temperature

2: H₂ / Pd/C / methanol

3: water soluble carbodiimide hydrochloride, HOBt, DMAP, TEA / dimethylformamide / Ambient temperature

4: H₂ / Pd/C / methanol

5: Et₃N / CH₂Cl₂

With dmap; TEA; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.46.697

upstream raw materials:

Cbz-D-Phe

tert-butyl 3-aminopropanoate hydrochloride

3-((R)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-propionic acid tert-butyl ester

(S)-2-[(R)-1-(2-tert-Butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Downstream raw materials:

((S)-2-{(R)-1-[2-(3-Carboxymethoxy-phenylcarbamoyl)-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-pyrrolidin-1-yl)-oxo-acetic acid methyl ester

((S)-2-{(R)-1-[2-(2-Carboxymethoxy-phenylcarbamoyl)-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-pyrrolidin-1-yl)-oxo-acetic acid methyl ester

((S)-2-{(R)-1-[2-(3-tert-Butoxycarbonylmethoxy-phenylcarbamoyl)-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-pyrrolidin-1-yl)-oxo-acetic acid methyl ester

((S)-2-{(R)-1-[2-(2-tert-Butoxycarbonylmethoxy-phenylcarbamoyl)-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-pyrrolidin-1-yl)-oxo-acetic acid methyl ester

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