Benzyl L-leucinate → N-t-butoxycarbonylglycyl-L-leucine benzyl ester

HRID 372783Notes

Reaction equation

HRID 372783 reaction equation
ClC1C=C(Cl)C(Cl)=CC=1[O:10][C:11](=O)[CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[CH2:22]([O:29][C:30](=[O:37])[C@H:31]([CH2:33][CH:34]([CH3:36])[CH3:35])[NH2:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][C:30](=[O:37])[C@H:31]([CH2:33][CH:34]([CH3:35])[CH3:36])[NH:32][C:11](=[O:10])[CH2:12][NH:13][C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6451313Benzyl L-leucinateHCID 12799284t-Butoxycarbonylglycine-2,4,5-Trichlorophenyl Ester

Product 1

HCID 53703413N-t-butoxycarbonylglycyl-L-leucine benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 19.5 parts N-t-butoxycarbonylglycine 2,4,5-trichlorophenyl ester and 11.1 parts L-leucine benzyl ester in 200 parts methylene chloride is stirred overnight at room temperature. The solvent is then removed by evaporation under reduced pressure. The crude dipeptide is then subjected to low-pressure column chromatography on silica gel to afford N-t-butoxycarbonylglycyl-L-leucine benzyl ester.

Workup

  1. customThe solvent is then removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-0ac71ffc126449cab9a5591baaaff651
Source dataset
uspto-grants-1978_05
Patent number
US04092304

Reaction notes

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