(1-{1-[6-(3,4-Difluoro-phenoxy)-4-(tetrahydro-pyran-4-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester → N-{1-[6-(3,4-Difluoro-phenoxy)-4-(tetrahydro-pyran-4-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-2-methylamino-propionamide

Participants

Reaction Steps

The Cbz-protected intermediate 27 (160 mg, 0.24 mmol) was stirred vigorously with 10% Pd-on-carbon (wet, 100 mg, 0.09 mmol) in MeOH (20 mL) under 1 atm H2. After 4 h, 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, 10-55% ACN/water containing 0.1% HOAc over 20 min; Flow: 40 mL/min) to afford 70 mg of 28 (45%, 3 steps) as a flocculent, white solid following lyophilization.

Provenance & Evidence