3-tert-butoxycarbonylamino-pyrrolidine-1-carboxylic acid 4-nitro-phenyl ester

Base Information

• Chemical Name: 3-tert-butoxycarbonylamino-pyrrolidine-1-carboxylic acid 4-nitro-phenyl ester
• CAS No.: 764722-58-9
• Molecular Formula: C₁₆H₂₁N₃O₆
• Molecular Weight: 351.359
• Mol file: 764722-58-9.mol

Synonyms:3-tert-butoxycarbonylamino-pyrrolidine-1-carboxylic acid 4-nitro-phenyl ester

Chemical Property of 3-tert-butoxycarbonylamino-pyrrolidine-1-carboxylic acid 4-nitro-phenyl ester

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of 3-tert-butoxycarbonylamino-pyrrolidine-1-carboxylic acid 4-nitro-phenyl ester

There total 1 articles about 3-tert-butoxycarbonylamino-pyrrolidine-1-carboxylic acid 4-nitro-phenyl 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: 83.0%

4-Nitrophenyl chloroformate (7693-46-1) + 3-N-tert-butoxycarbonyl-3-(R)-aminopyrrolidine (122536-77-0,140629-77-2) → 3-tert-butoxycarbonylamino-pyrrolidine-1-carboxylic acid 4-nitro-phenyl ester (764722-58-9)

Guidance literature:

With TEA; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2006.06.045

Reference yield:

3-tert-butoxycarbonylamino-pyrrolidine-1-carboxylic acid 4-nitro-phenyl ester (764722-58-9) + 4'-Trifluoromethyl-biphenyl-4-carboxylic acid methyl-(S)-pyrrolidin-3-yl-amide (762285-68-7) → ((R)-1-{(S)-3-[Methyl-(4'-trifluoromethyl-biphenyl-4-carbonyl)-amino]-pyrrolidine-1-carbonyl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester (764722-59-0)

Guidance literature:

With dmap; TEA; In N,N-dimethyl-formamide; at 100 ℃; for 12h;

DOI:10.1016/j.bmcl.2006.06.045

Reference yield:

3-tert-butoxycarbonylamino-pyrrolidine-1-carboxylic acid 4-nitro-phenyl ester (764722-58-9) → 4'-Trifluoromethyl-biphenyl-4-carboxylic acid methyl-{(S)-1-[(R)-3-(4,4,4-trifluoro-butylamino)-pyrrolidine-1-carbonyl]-pyrrolidin-3-yl}-amide

Guidance literature:

Multi-step reaction with 3 steps

1: 4-N,N-dimethylaminopyridine; TEA / dimethylformamide / 12 h / 100 °C

2: TFA / CH₂Cl₂ / 1 h / 20 °C

3: NaI; K₂CO₃ / dimethylformamide / 3 h / 80 °C

With dmap; TEA; potassium carbonate; trifluoroacetic acid; sodium iodide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.06.045

upstream raw materials:

4-Nitrophenyl chloroformate

3-N-tert-butoxycarbonyl-3-(R)-aminopyrrolidine

Downstream raw materials:

((R)-1-{(S)-3-[Methyl-(4'-trifluoromethyl-biphenyl-4-carbonyl)-amino]-pyrrolidine-1-carbonyl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester