Réaction #2045047

ord-b81560174907434db5df712b633fb9d4

Équation de réaction

COC(=O)COc1ccc(NC(=O)COCc2ccccc2)cc1
4-(2-Benzyloxyacetylamino)-phenoxyacetic acid methyl ester
COC(=O)COc1ccc(NC(=O)COCc2ccccc2)cc1
4-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl ester
COC(=O)COc1ccc(NC(=O)CO)cc1
67
Rendement 77.0%
COC(=O)COc1ccc(NC(=O)CO)cc1
4-(2-Hydroxyacetylamino)phenoxyacetic acid methyl ester
Rendement 77.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreCatalyst was removed by filtration and methanol
  2. 2
    workup.DISTILLATIONdistilled off
  3. 3
    AutreCrude 67 was recrystallised in chloroform:hexane (1:6)

Mode opératoire

4-(2-Benzyloxyacetylamino)-phenoxyacetic acid methyl ester 66 (25 g, 76 mmol) was dissolved in methanol (450 ml) in a pressure vessel, palladium on carbon (5%, 10 g) added and the mixture stirred under a hydrogen atm. (2 Kg) for 5 hrs. Catalyst was removed by filtration and methanol distilled off. Crude 67 was recrystallised in chloroform:hexane (1:6) to give pure 67 (14 g) as a white powder. M.p: 147.5-150° C.

Source

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