Methylamine → 3-Benzyloxycarbonylamino-2,2-dimethyl-N-methylpropionic acid amide

HRID 744842Notes

Reaction equation

HRID 744842 reaction equation
C([O:3][C:4](=O)[C:5]([CH3:19])([CH3:18])[CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])C.[CH3:21][NH2:22]>>[CH2:11]([O:10][C:8]([NH:7][CH2:6][C:5]([CH3:19])([CH3:18])[C:4]([NH:22][CH3:21])=[O:3])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 22364460Ethyl 3-(((benzyloxy)carbonyl)amino)-2,2-dimethylpropanoate

Product 1

HCID 223644803-Benzyloxycarbonylamino-2,2-dimethyl-N-methylpropionic acid amide

Procedure

4.19 g of 3-benzyloxycarbonylamino-2,2-dimethylpropionic acid ethyl ester and 50 ml of 33% methylamine (in ethanol) are stirred for 8 days at 60° C. in a bomb tube. The reaction mixture is concentrated by evaporation and the residue is purified by FC (220 g of silica gel, dichloromethane/methanol=95:5). The title compound is obtained: Rf (dichloromethane/methanol=9:1)=0.51.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. customthe residue is purified by FC (220 g of silica gel, dichloromethane/methanol=95:5)

Sources & evidence

ORD record
ord-df5891795cd442b8b28a9e516d561b26
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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