(1-{1-Cyclohexyl-2-[4-cyclopropanecarbonyl-6-(1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethylcarbamoyl}-ethyl) methyl-carbamic benzyl ester → 4-[2-Cyclohexyl-2-(2-methylamino-propionylamino)-acetyl]-1-cyclopropanecarbonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide

Participants

Reaction Steps

A mixture of 48 (450 mg, 0.63 mmol) and 10% palladium-on-carbon (wet, 90 mg) in MeOH (15 mL) was shaken at 50 psi under a H2 atmosphere. After 1.5 h, the mixture was filtered through a 0.45 μM filtering disc, washed with MeOH and concentrated. Purification by reverse-phase HPLC (2″ Dynamax® C18, 10-70% ACN in H2O with 0.1% HOAc over 30 min) afforded 49 (123 mg) as a white flocculent solid following lyophilization of the purified fractions.

Provenance & Evidence