Benzyl carbamate → 2-(((Benzyloxy)carbonyl)amino)-2-hydroxyacetic acid

HRID 1080375Notes

Reaction equation

HRID 1080375 reaction equation
[C:1](=[O:11])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:2].O.[C:13]([OH:17])(=[O:16])[CH:14]=[O:15]>CCOCC>[OH:15][CH:14]([C:13]([OH:17])=[O:16])[NH:2][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:11]

Participants

4

Reactant 2

HCID 12136Benzyl carbamateHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 35095062-(((Benzyloxy)carbonyl)amino)-2-hydroxyacetic acidYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Benzyl carbamate (63 g, 0.05 mol) was stirred with glyoxylic acid monohydrate (5.09 g, 0.055 mol) in dry ether (50 mL). The crystalline product 22A (7.81 g, 73%) formed was filtered and washed with ether.

Sources & evidence

ORD record
ord-7e6840bf69e24898a2e2e56b7bbabc26
Source dataset
uspto-grants-1996_12
Patent number
US05580979

Reaction notes

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