3-Benzyloxy-4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-benzoic acid methyl ester → 4-((S)-2-tert-Butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-3-hydroxy-benzoic acid methyl ester

Participants

Reaction Steps

A solution of 3-benzyloxy-4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-benzoic acid methyl ester (7.40 g, 15.0 mmol) in EtOH (100 mL) was shaken with 20% Pd/C (1.0 g) under H2 (50 psi) for 1.5 h using a Parr apparatus. The reaction mixture was filtered through celite and concentrated. 4-((S)-2-tert-Butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-3-hydroxy-benzoic acid methyl ester was obtained (6.03 g, 99%) as an off white foam. MS m/z 401.2 (M−1).

Provenance & Evidence