Réaction #2045014

ord-7258ec19e4254638922bdf06c4638940

Équation de réaction

CC(=O)Nc1ccc(OC(=O)COCc2ccccc2)cc1
Benzyloxyacetic acid 4-acetylamino-phenyl ester
CC(=O)Nc1ccc(OC(=O)COCc2ccccc2)cc1
Benzyloxy-acetic acid 4-acetylamino-phenyl ester
CC(=O)Nc1ccc(OC(=O)CO)cc1
25
Rendement 57.4%
CC(=O)Nc1ccc(OC(=O)CO)cc1
Hydroxy-acetic acid 4-acetylamino-phenyl ester
Rendement 57.4%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe catalyst was removed by filtration
  2. 2
    workup.DISTILLATIONthe methanol was then distilled off
  3. 3
    AutreThe crude 25 was recrystallized from mixture of chloroform:methanol (1:4)

Mode opératoire

Benzyloxyacetic acid 4-acetylamino-phenyl ester 24 (15 g, 50 mmol) was dissolved in methanol (150 ml) in a pressure vessel, palladium on carbon (5%, 8 grams) added and the mixture stirred under an atmosphere of hydrogen (3 Kg) for 20 hours. The catalyst was removed by filtration and the methanol was then distilled off. The crude 25 was recrystallized from mixture of chloroform:methanol (1:4) to get pure 25 (6 g, 57.2%) as a white powder. M.p: 144-146° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08409559B2uspto-grants-2013_04