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

HRID 280494Notes

Reaction equation

HRID 280494 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

5

Reactant 3

HCID 962WaterHCID 12136Benzyl carbamateHCID 70211Ethyl oxoacetate

Product 1

HCID 20233481Ethyl 2-(benzyloxycarbonylamino)-2-(hydroxy)acetateYield 64.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated in vacuo, and diethyl ether
  3. additionwas added to the residue
  4. filtrationThe mixture was filtered
  5. customthe diethyl ether solution was evaporated in vacuo

Sources & evidence

ORD record
ord-b20c633cf15b48ea8d55b44898ba85f5
Source dataset
uspto-grants-1986_05
Patent number
US04590073

Reaction notes

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