(S)-2-((R)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl ester

Base Information

• Chemical Name: (S)-2-((R)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl ester
• CAS No.: 220569-40-4
• Molecular Formula: C₂₂H₂₆N₂O₃
• Molecular Weight: 366.46
• Mol file: 220569-40-4.mol

Synonyms:(S)-2-((R)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl ester

Chemical Property of (S)-2-((R)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((R)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl ester

There total 5 articles about (S)-2-((R)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl 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: 91.0%

(2S,3S)-2-(3-benzyl-3-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl ester (220569-33-5) → (S)-2-((R)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl ester (220569-40-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0968-0896(98)80022-9

Reference yield:

(2S,4S)-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (191980-50-4) → (S)-2-((R)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl ester (220569-40-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / -78 °C

1.2: 77 percent / tetrahydrofuran; toluene / 16 h / -78 - 25 °C

2.1: ozone; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

2.2: 95 percent / Me₂S / CH₂Cl₂; methanol / -78 - 25 °C

3.1: NaOAc; 4 Angstroem molecular sieves; NaCNBH₃ / methanol / 25 °C

4.1: 697 mg / 1-hydroxybenzotriazole / toluene / 16 h / Heating

5.1: 91 percent / hydrogen / Pd/C / ethanol

With 4 A molecular sieve; hydrogen; sodium acetate; potassium hexamethylsilazane; sodium cyanoborohydride; sodium hydrogencarbonate; benzotriazol-1-ol; ozone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1.1: Metallation / 1.2: Alkylation / 2.1: ozonolysis / 2.2: Reduction / 3.1: Alkylation / 4.1: Cyclization / 5.1: Hydrogenolysis;

DOI:10.1016/S0968-0896(98)80022-9

Reference yield:

(2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester (220569-30-2) → (S)-2-((R)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl ester (220569-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOAc; 4 Angstroem molecular sieves; NaCNBH₃ / methanol / 25 °C

2: 697 mg / 1-hydroxybenzotriazole / toluene / 16 h / Heating

3: 91 percent / hydrogen / Pd/C / ethanol

With 4 A molecular sieve; hydrogen; sodium acetate; sodium cyanoborohydride; benzotriazol-1-ol; palladium on activated charcoal; In methanol; ethanol; toluene; 1: Alkylation / 2: Cyclization / 3: Hydrogenolysis;

DOI:10.1016/S0968-0896(98)80022-9

upstream raw materials:

(2S,3S)-2-(3-benzyl-3-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl ester

(2S,4S)-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

(2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

(2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

(2S,3S)-N-[3-benzyl-1-(1-hydroxymethyl-3-phenylpropyl)-2-oxo-pyrrolidin-3-yl]-benzene-sulfonamide

(2S,3S)-2-(3-benzenesulfonylamino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenylbutyric acid methyl ester