Glyoxylic Acid → Alpha-Hydroxyhippuric acid

HRID 20188

Reaction equation

HRID 20188 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([OH:14])(=[O:13])[CH:11]=[O:12]>CC(C)=O>[C:1]([NH:9][CH:11]([OH:12])[C:10]([OH:14])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 760Glyoxylic AcidHCID 2331Benzamide

Product 1

HCID 450272Alpha-Hydroxyhippuric acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of commercially available benzamide 35 and glyoxylic acid 41 was heated at reflux in acetone to give pure N-benzoyl-2-hydroxyglycine 65 as a colourless solid in quantitative yield (Scheme 4.12). The 1H n.m.r. spectrum supported formation of the ox-hydroxyglycine derivative 65 with the appearance of a methine (H2) doublet and broad amide (NH) doublet at δ 5.60 and δ 9.26 respectively. Spectroscopic data were in agreement with those reported in the literature.209

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-9b741076ad9544a8b379ce92eb9f70b0
Source dataset
uspto-grants-2010_06
Patent number
US07745573B2

Linked notes

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