Reaction #2045051

Reaction equation

6-[4-(2-Benzyloxyacetylamino)phenoxy]hexanoic acid methyl ester

→

71

Yield 65.3%

6-[4-(2-Hydroxyacetylamino)phenoxy]hexanoic acid methyl ester

Yield 65.3%

Solvents

methanol

Conditions

Workup

1. 1
   OtherCatalyst was removed by filtration and methanol
2. 2
   workup.DISTILLATIONwas distilled off
3. 3
   OtherCrude 71 was recrystallised in chloroform:hexane (1:6)

Procedure

6-[4-(2-Benzyloxyacetylamino)phenoxy]hexanoic acid methyl ester 70 (1 g, 2.6 mmol) was dissolved in methanol (10 ml) in a pressure vessel, pd on carbon (5%, 250 mg) added and the mixture stirred under a hydrogen atm. (2 Kg) for 5 hrs. Catalyst was removed by filtration and methanol was distilled off. Crude 71 was recrystallised in chloroform:hexane (1:6) to get pure 71 (0.5 g, 65.3%) as a white powder. M.p: 91.5-94° C.

Source