Triethylamine → N-benzyloxycarbonyl-N-allyl-D-alanine t-butyl ester

HRID 1755827Notes

Reaction equation

HRID 1755827 reaction equation
[C:1]([O:5][C:6](=[O:13])[C@@H:7]([CH3:12])[NH:8][CH2:9][CH:10]=[CH2:11])([CH3:4])([CH3:3])[CH3:2].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:13])[C@@H:7]([CH3:12])[N:8]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:9][CH:10]=[CH2:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 54332184N-allyl-D-alanine t-butyl ester

Product 1

HCID 54427579N-benzyloxycarbonyl-N-allyl-D-alanine t-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Allyl-D-alanine t-butyl ester (69) is treated with 1.1 equivalents of benzyl chloroformate and 1.1 equivalents of triethylamine in methylene chloride at room temperature overnight. After evaporation of solvent, the product is purified by silica gel chromatography to give (70).

Workup

  1. customAfter evaporation of solvent
  2. customthe product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-2959b5d665364fc0820cbc1a7f2c17b0
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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