Water → Ethyl 2-(benzyloxycarbonylamino)-2-(hydroxy)acetate

Reaction equation

[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[O:3].[C:8](=[O:18])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:9].O>C1(C)C=CC=CC=1>[CH2:11]([O:10][C:8]([NH:9][CH:2]([OH:3])[C:1]([O:5][CH2:6][CH3:7])=[O:4])=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Procedure

A solution of 17.3 g (0.169 mole) of ethyl glyoxylate and 23.0 g (0.152 mole) of benzyl carbamate in 250 ml of toluene was heated under reflux for 6 hours, with removal of water using a Dean-Stark trap. The resulting reaction mixture was concentrated in vacuo, and diethyl ether was added to the residue. The mixture was filtered, and the diethyl ether solution was evaporated in vacuo to give 25.0 g of ethyl 2-(benzyloxycarbonylamino)-2-(hydroxy)acetate as a sticky solid.