Reacción #2045054

ord-6cd49050e6f4430f83d6887c11fd25e2

Ecuación de reacción

COC(=O)C(C)Oc1ccc(NC(=O)CCCCCOCc2ccccc2)cc1
2-[4-(6-Benzyloxyhexanoylamino)phenoxy]propionic acid methyl ester
COC(=O)C(C)Oc1ccc(NC(=O)CCCCCO)cc1
79
Rendimiento 51.6%
COC(=O)C(C)Oc1ccc(NC(=O)CCCCCO)cc1
2-[4-(6-Hydroxyhexanoylamino)phenoxy]propionic acid methyl ester
Rendimiento 51.6%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroCatalyst was removed by filtration and methanol
  2. 2
    workup.DISTILLATIONdistilled off
  3. 3
    OtroThe crude 79 was purified by column chromatography on silica gel

Procedimiento

2-[4-(6-Benzyloxyhexanoylamino)phenoxy]propionic acid methyl ester 78 (15 g, 37.59 mmol) was dissolved in methanol (150 ml) in a pressure vessel, palladium on carbon (50% wet, 5%, 15 g) added and the mixture stirred under a hydrogen atmosph. (4 Kg) for 16 hrs. Catalyst was removed by filtration and methanol distilled off. The crude 79 was purified by column chromatography on silica gel using chloroform as eluant to get pure 79 (6 g, 51.6%) as a white powder. M.p: 62-64.5° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08409559B2uspto-grants-2013_04