Methanol → 3-Benzyloxycarbonylamino-2(r,s)-methylpropionic acid methyl ester

HRID 725654Notes

Reaction equation

HRID 725654 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH:13]([CH3:17])[C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]O>S(=O)(=O)(O)O>[CH3:18][O:15][C:14](=[O:16])[CH:13]([CH3:17])[CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

4

Reactant 2

HCID 887MethanolHCID 3042743-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid

Product 1

HCID 223644703-Benzyloxycarbonylamino-2(r,s)-methylpropionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

22.6 g of 3-benzyloxycarbonylamino-2(R,S)-methylpropionic acid are left to stand for 24 hours in 230 ml of methanol with a few drops of concentrated sulfuric acid. The reaction mixture is concentrated by evaporation and the residue is purified by FC (220 g of silica gel, dichloromethane). The title compound is obtained: Rf (dichloromethane/methanol=95:5)=0.60.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. customthe residue is purified by FC (220 g of silica gel, dichloromethane)

Sources & evidence

ORD record
ord-18c0112f68d94854aba446acbd1a5ee1
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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