Benzoic acid 1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-3-yl ester

Base Information

• Chemical Name: Benzoic acid 1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-3-yl ester
• CAS No.: 204381-53-3
• Molecular Formula: C₂₅H₃₀N₂O₅
• Molecular Weight: 438.524

Synonyms:Benzoic acid 1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-3-yl ester

Chemical Property of Benzoic acid 1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-3-yl ester

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Technology Process of Benzoic acid 1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-3-yl ester

There total 2 articles about Benzoic acid 1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-3-yl 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: 84.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + benzoic acid pirrolidin-3-yl ester (51285-23-5) → Benzoic acid 1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-3-yl ester (204381-53-3)

Guidance literature:

With TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane;

DOI:10.1016/S0960-894X(98)00006-7

Reference yield:

tert-butyl 3-(benzoyloxy)pyrrolidine-1-carboxylate (204381-51-1) → Benzoic acid 1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-3-yl ester (204381-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / TFA / CH₂Cl₂

2: 84 percent / BOP, TEA / CH₂Cl₂

With TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0960-894X(98)00006-7

Reference yield: 90.0%

Benzoic acid 1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-3-yl ester (204381-53-3) → 1-[(tert-butoxycarbonyl)-L-phenylalanyl]-3(R,S)-pyrrolidinol (186431-54-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran;

DOI:10.1016/S0960-894X(98)00006-7

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

benzoic acid pirrolidin-3-yl ester

tert-butyl 3-(benzoyloxy)pyrrolidine-1-carboxylate

Downstream raw materials:

1-[(tert-butoxycarbonyl)-L-phenylalanyl]-3(R,S)-pyrrolidinol

1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidin-3-one

(S)-2-Amino-1-(3-hydroxy-pyrrolidin-1-yl)-3-phenyl-propan-1-one

N-(N-nicotinoyl-L-phenylalanyl)pyrrolidin-3-one

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