(2S,4S)-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester → 1-hydroxy-naphthalene-2-carboxylic acid ((3S,5S)-5-oxazol-2-yl-pyrrolidin-3-yl)-amide

Participants

Reaction Steps

To a solution of (2S,4S)-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester (30 mg, 0.06 mmol) in methanol (2 mL) was added 20% Pd(OH)2 (20 mg) and the mixture was stirred at room temp. for 16 h. with a balloon containing H2 gas. The reaction mixture was then filtered and concentrated under reduced pressure to give 1-hydroxy-naphthalene-2-carboxylic acid ((3S,5S)-5-oxazol-2-yl-pyrrolidin-3-yl)-amide (15 mg) as a light brown liquid. MS calcd. for C18H18N3O3[(M+H)+] 324, obsd. 324.

Provenance & Evidence