methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionyl>-L-phenylalaninate

Base Information

Chemical Name:methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionyl>-L-phenylalaninate
CAS No.:117162-21-7
Molecular Formula:C₃₈H₃₉N₃O₆
Molecular Weight:633.744
Hs Code.:

Synonyms:methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionyl>-L-phenylalaninate

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Chemical Property of methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionyl>-L-phenylalaninate

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Technology Process of methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionyl>-L-phenylalaninate

There total 7 articles about methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionyl>-L-phenylalaninate 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: 88.0%

: 7524-50-7
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

: 117162-17-1
2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionic acid

: 117162-21-7
methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionyl>-L-phenylalaninate

Guidance literature:: With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; 1.) -23 deg C, 2 h, 2.) RT, overnight;
DOI:10.1021/jo00259a003

Reference yield:

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

: 117162-21-7
methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionyl>-L-phenylalaninate

Guidance literature:: Multi-step reaction with 8 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: LiOH*H₂O / 1,2-dimethoxy-ethane; H₂O / 1 h / 0 - 20 °C

8: 88 percent / N-methylmorpholine, 1-hydroxybenzotriazole (HOBT), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 1.) -23 deg C, 2 h, 2.) RT, overnight

With diazomethane; 4-methyl-morpholine; lithium hydroxide; sodium hydroxide; dimethylsulfide; 4 A molecular sieve; sodium acetate; sodium hexamethyldisilazane; sodium cyanoborohydride; benzotriazol-1-ol; toluene-4-sulfonic acid; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00259a003

Reference yield:

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

: 117162-21-7
methyl <2(S)-<3-<(benzyloxycarbonyl)amino>-3-(phenylmethyl)-2-oxo-1-pyrrolidinyl>-3-phenylpropionyl>-L-phenylalaninate

Guidance literature:: Multi-step reaction with 7 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: LiOH*H₂O / 1,2-dimethoxy-ethane; H₂O / 1 h / 0 - 20 °C

7: 88 percent / N-methylmorpholine, 1-hydroxybenzotriazole (HOBT), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 1.) -23 deg C, 2 h, 2.) RT, overnight

With diazomethane; 4-methyl-morpholine; lithium hydroxide; sodium hydroxide; dimethylsulfide; 4 A molecular sieve; sodium acetate; sodium hexamethyldisilazane; sodium cyanoborohydride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00259a003