Reaction #2045053

Reaction equation

4-(6-Benzyloxyhexanoylamino)phenoxyacetic acid methyl ester

→

77

Yield 24.4%

4-(6-Hydroxyhexanoylamino)phenoxyacetic acid methyl ester

Yield 24.4%

Solvents

methanol

dimethylformamide

Conditions

Workup

1. 1
   OtherCatalyst was removed by filtration
2. 2
   workup.DISTILLATIONthe solvents were distilled off under vacuum
3. 3
   OtherCrude 77 was purified by column chromatography on silica gel

Procedure

4-(6-Benzyloxyhexanoylamino)phenoxyacetic acid methyl ester 76 (24 grams, 62.33 mmol) was dissolved in a mixture of methanol (200 ml) and dimethylformamide (50 ml) in a pressure vessel, palladium on carbon (5%, 15 g) was added and the mixture stirred under a hydrogen atm. (4 Kg) for 24 hrs. Catalyst was removed by filtration, and the solvents were distilled off under vacuum. Crude 77 was purified by column chromatography on silica gel using chloroform as eluant to get pure 77 (4.5 g, 24.4%) as a white powder. M.p: 87.5-90.4° C.

Source