Ethyl chloroformate → methyl 4-[N-(ethoxycarbonyl)aminoacetyl]-phenoxyacetate

HRID 2419375Notes

Reaction equation

HRID 2419375 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].Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>N1C=CC=CC=1>[CH2:22]([O:21][C:19]([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:20])[CH3:23]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 20315552Methyl 4-(aminoacetyl)phenoxyacetate hydrochloride

Product 1

HCID 53687822methyl 4-[N-(ethoxycarbonyl)aminoacetyl]-phenoxyacetateYield 79.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Pyridine (40ml.) was added to a stirred mixture of methyl 4-(aminoacetyl)phenoxyacetate hydrochloride (5.2g.) and ethyl chloroformate (2.3g.). An exothermic reaction occurred and was allowed to continue until a homogeneous solution was obtained. This solution was then cooled and the solid residue which formed was first separated, and then washed successively with ether (2 × 30ml.), water (2 × 30ml.) and ether (2 × 30ml.), before recrystallisation from toluene to give methyl 4-[N-(ethoxycarbonyl)aminoacetyl]-phenoxyacetate (4.7g.), m.p. 128°-129° C.

Workup

  1. customAn exothermic reaction
  2. customwas obtained
  3. temperatureThis solution was then cooled
  4. customthe solid residue which formed
  5. washwashed successively with ether (2 × 30ml.), water (2 × 30ml.) and ether (2 × 30ml.), before recrystallisation from toluene

Sources & evidence

ORD record
ord-c09b3f3a194e4fa796b8dd31d37ff585
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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