Acetamide → Acetamidoglycolic acid

HRID 20187

Reaction equation

HRID 20187 reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].[C:5]([OH:9])(=[O:8])[CH:6]=[O:7]>CC(C)=O>[C:1]([NH:4][CH:6]([OH:7])[C:5]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 178AcetamideHCID 760Glyoxylic Acid

Product 1

HCID 14212846Acetamidoglycolic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of commercially available acetamide 34 and glyoxylic acid 41 was heated at reflux in acetone to give pure N-acetyl-2-hydroxyglycine 42 as a viscous yellow oil in quantitative yield. The 1H n.m.r. spectrum supported formation of the α-hydroxyglycine derivative 42 with the appearance of a methine (H2) doublet and broad amide (NH) doublet at δ 5.39 and δ 8.65 respectively. Spectroscopic data were in agreement with those reported in the literature.195

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-e76f8a57f7894eaca8797727c758d1d0
Source dataset
uspto-grants-2010_06
Patent number
US07745573B2

Linked notes

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