1-{[(S)-2-(3-Trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carbonyl]-amino}-indolizine-3-carboxylic acid benzyl ester → 1-{[(S)-2-(3-Trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carbonyl]-amino}-indolizine-3-carboxylic acid

Participants

Reaction Steps

To 1-{[(S)-2-(3-Trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carbonyl]-amino}-indolizine-3-carboxylic acid benzyl ester (100 mg, 0.177 mmol) dissolved in THF (3 mL) was added Pd/C 10% (20 mg). Air was removed from the flask under vacuum and replaced with nitrogen three times, finally nitrogen was removed and replaced with hydrogen and the mixture was stirred at RT for 5 h. Hydrogen was removed and replaced by nitrogen, the catalyst was removed by filtration through a pad of Celite and washed with THF. Solvents were concentrated to give a mixture containing the desired compound contaminated with 20% of the decarboxylated analog. The mixture was used without further purification in the next step. LC/MS: 475 [M−H]−; tR (HPLC conditions a): 3.41 min.

Provenance & Evidence