(1-{1-[4-Benzylcarbamoyl-6-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester → HCID 67607310, compound

Participants

Reaction Steps

A solution containing 50 (0.53 mmol) and NH4OAc (25 mg, 0.27 mmol) in MeOH (10 mL) was treated with 10% Pd-on-carbon (wet, 60 mg, 0.05 mmol) and the stirred mixture was purged with hydrogen. After 1 h stirring under a balloon of hydrogen, TLC analysis (10:1 DCM/MeOH) indicated the reaction was complete. The catalyst was removed by filtration with an Acrodisc® 0.45 μm nylon membrane syringe filter and the solvent was removed in vacuo. The crude product was purified by reverse-phase HPLC (2″ Dynamax® C18, 10-60% ACN/water containing 0.1% HOAc over 25 min; Flow: 40 mL/min). Fractions containing pure product were combined, frozen, and lyophilized to provide 251 mg (84%, 2 steps) of 51 as a floculent white powder.

Provenance & Evidence