Trimethyl orthoformate → methyl 4-[(N-formyl)aminoacetyl]phenoxyacetate

HRID 2419379Notes

Reaction equation

HRID 2419379 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)=[O:5].[CH:18](OC)(OC)[O:19]C>>[CH:18]([NH:2][CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1)=[O:5])=[O:19]

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 20315552Methyl 4-(aminoacetyl)phenoxyacetate hydrochloride

Product 1

HCID 20315613methyl 4-[(N-formyl)aminoacetyl]phenoxyacetate

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-(aminoacetyl)phenoxyacetate hydrochloride (2.6g.) and trimethyl orthoformate (3.18g.) was stirred at 100° C. for 1 hour under reflux. The volatile reaction products were then allowed to distil off. The yellow residual oil thus obtain crystallised on cooling to give methyl 4-[(N-formyl)aminoacetyl]phenoxyacetate as a solid (2.2g.), m.p. 116° C., after recrystallisation from methanol.

Workup

  1. temperatureunder reflux
  2. customto distil off
  3. customThe yellow residual oil thus obtain
  4. customcrystallised
  5. temperatureon cooling

Sources & evidence

ORD record
ord-98f6269932f3487e92edcb900106ee53
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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