4-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl ester → 4-(2-Hydroxyacetylamino)phenoxyacetic acid methyl ester

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Reaction Steps

[4-(2-Benzyloxyacetylamino)phenoxy]acetic acid methyl ester 49 (25 g, 76 mmol) was dissolved in methanol (450 ml) in a pressure vessel. Palladium on carbon (5%, 10 g) was added and the mixture stirred under a hydrogen atmosphere (2 kg) for 5 hrs. Catalyst was removed by filtration and methanol distilled off. Crude 50 was recrystallised in chloroform:hexane (1:6) to give pure 50 (14 g) as a white powder with an m.p. between 147.5-150° C.

Provenance & Evidence