2(S)-methyl 2-<3-amino-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionate

Base Information

Chemical Name:2(S)-methyl 2-<3-amino-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionate
CAS No.:117162-19-3
Molecular Formula:C₂₁H₂₄N₂O₃
Molecular Weight:352.433
Hs Code.:

Synonyms:2(S)-methyl 2-<3-amino-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionate

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Chemical Property of 2(S)-methyl 2-<3-amino-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionate

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Technology Process of 2(S)-methyl 2-<3-amino-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionate

There total 7 articles about 2(S)-methyl 2-<3-amino-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionate 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: 92.0%

: 117162-09-1,117183-54-7
(2S)-methyl 2-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionate

: 117162-19-3
2(S)-methyl 2-<3-amino-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionate

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; for 3.5h; under 735.5 Torr; Ambient temperature;
DOI:10.1021/jo00259a003

Reference yield:

: 1161-13-3
N-Cbz-L-Phe

: 117162-19-3
2(S)-methyl 2-<3-amino-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionate

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / p-TsOH / toluene / Heating

2: 1.) sodium hexamethyldisilyl amide / 1.) THF, toluene. -78 deg C, 0.5 h

3: 1.) NaOH, 2.) CH₂N₂ / 1.) EtOH, H₂O, reflux, 1 h, 2.) Et₂O, from 0 to RT, 1 h

4: 1.) O₃, 2.) methyl sulfide (DMS) / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 to 0 deg C

5: 1.17 g / AcONa, NaCNBH₃, molecular sieves 4A / methanol / Ambient temperature

6: 1-hydroxybenzotriazole (HOBT) / toluene; 1,2-dimethoxy-ethane / 100 °C

7: 92 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol / 3.5 h / 735.5 Torr / Ambient temperature

With diazomethane; sodium hydroxide; dimethylsulfide; 4 A molecular sieve; hydrogen; sodium acetate; sodium hexamethyldisilazane; sodium cyanoborohydride; benzotriazol-1-ol; toluene-4-sulfonic acid; ozone; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; ethyl acetate; toluene;
DOI:10.1021/jo00259a003

Reference yield:

: 55740-07-3
(4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester

: 117162-19-3
2(S)-methyl 2-<3-amino-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) sodium hexamethyldisilyl amide / 1.) THF, toluene. -78 deg C, 0.5 h

2: 1.) NaOH, 2.) CH₂N₂ / 1.) EtOH, H₂O, reflux, 1 h, 2.) Et₂O, from 0 to RT, 1 h

3: 1.) O₃, 2.) methyl sulfide (DMS) / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 to 0 deg C

4: 1.17 g / AcONa, NaCNBH₃, molecular sieves 4A / methanol / Ambient temperature

5: 1-hydroxybenzotriazole (HOBT) / toluene; 1,2-dimethoxy-ethane / 100 °C

6: 92 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol / 3.5 h / 735.5 Torr / Ambient temperature

With diazomethane; sodium hydroxide; dimethylsulfide; 4 A molecular sieve; hydrogen; sodium acetate; sodium hexamethyldisilazane; sodium cyanoborohydride; benzotriazol-1-ol; ozone; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; ethyl acetate; toluene;
DOI:10.1021/jo00259a003