Reaction #2045054

Reaction equation

2-[4-(6-Benzyloxyhexanoylamino)phenoxy]propionic acid methyl ester

→

79

Yield 51.6%

2-[4-(6-Hydroxyhexanoylamino)phenoxy]propionic acid methyl ester

Yield 51.6%

Solvents

methanol

Conditions

Workup

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

Procedure

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.

Source