(2S,4R)-2-[((R)-1-Carboxy-3-methyl-butyl)-methyl-carbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,4R)-2-[((R)-1-Carboxy-3-methyl-butyl)-methyl-carbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:161708-36-7
Molecular Formula:C₂₀H₂₈N₂O₆
Molecular Weight:392.452
Hs Code.:

Synonyms:(2S,4R)-2-[((R)-1-Carboxy-3-methyl-butyl)-methyl-carbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,4R)-2-[((R)-1-Carboxy-3-methyl-butyl)-methyl-carbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,4R)-2-[((R)-1-Carboxy-3-methyl-butyl)-methyl-carbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

There total 10 articles about (2S,4R)-2-[((R)-1-Carboxy-3-methyl-butyl)-methyl-carbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid benzyl 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:

: 28862-79-5
Z-D-Leu-OH

: 161708-36-7
(2S,4R)-2-[((R)-1-Carboxy-3-methyl-butyl)-methyl-carbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / KOH, Bu₄N(+)HSO₄(-) / tetrahydrofuran

2: 78 percent / Et₃N, DCC, DMAP / CH₂Cl₂ / 22 h / Ambient temperature

3: 98 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / 5 h / 2068.6 Torr

4: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH₂Cl₂, -15 deg C, 30 min, 2.) 0 deg C, 6 h

5: TBAF / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) r.t., 1 h

With 4-methyl-morpholine; dmap; potassium hydroxide; tetrabutyl ammonium fluoride; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1021/jo00097a022

Reference yield:

: 65635-85-0
N-methyl-N-(benzyloxycarbonyl)-D-leucine

: 161708-36-7
(2S,4R)-2-[((R)-1-Carboxy-3-methyl-butyl)-methyl-carbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / Et₃N, DCC, DMAP / CH₂Cl₂ / 22 h / Ambient temperature

2: 98 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / 5 h / 2068.6 Torr

3: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH₂Cl₂, -15 deg C, 30 min, 2.) 0 deg C, 6 h

4: TBAF / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) r.t., 1 h

With 4-methyl-morpholine; dmap; tetrabutyl ammonium fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1021/jo00097a022

Reference yield:

: 129919-93-3
N-<(benzyloxy)carbonyl>-N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester

: 161708-36-7
(2S,4R)-2-[((R)-1-Carboxy-3-methyl-butyl)-methyl-carbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / 5 h / 2068.6 Torr

2: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH₂Cl₂, -15 deg C, 30 min, 2.) 0 deg C, 6 h

3: TBAF / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) r.t., 1 h

With 4-methyl-morpholine; tetrabutyl ammonium fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate;
DOI:10.1021/jo00097a022