Reaction #2045049

Reaction equation

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

→

69

Yield 36.3%

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

Yield 36.3%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe catalyst was removed by filtration
2. 2
   workup.DISTILLATIONthe methanol distilled off
3. 3
   OtherThe crude 69 was recrystallised in chloroform:hexane (1:6)

Procedure

2-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl ester 68 (15 grams, 43.7 mmol) was dissolved in methanol (150 ml) in a pressure vessel, palladium on carbon (5%, 8 g) added and the mixture stirred under a hydrogen atmosphere (2.5 Kg) for 10 hrs. The catalyst was removed by filtration and the methanol distilled off. The crude 69 was recrystallised in chloroform:hexane (1:6) to give pure 69 (4 g, 36.3%) as a white powder. M.p: 111-112.6° C.

Source