2-[3-(S)-Benzyloxycarbonylamino-2-oxo-pyrrolidin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester → 2-[3-(S)-Amino-2-oxo-pyrrolidin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

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Reaction Steps

2-[3-(S)-Benzyloxycarbonylamino-2-oxo-pyrrolidin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (2.8 g, 6.0 mmol) in HCO2H/MeOH (30 mL, 4.4% solution) is quickly added via cannula to a solution of palladium black (2.0 g, 18.8 mmol) in water (1 ml,). After ca. 40 min the catalyst is filtered through Celite and basified with saturated sodium bicarbonate solution. The filtrate is concentrated in vacuo to remove methanol then the resulting solution is extracted with methylene chloride. The organic layer is washed with brine, dried over MgSO4, filtered and concentrated to dryness. The resulting white solid can be used in the subsequent step without further purification. The title compound was purified in the following manner to prepare a focused sulfonamide library. The crude solid was purified by RP-HPLC eluting with a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN. The appropriate fractions are combined and neutralized with saturated sodium bicarbonate solution then concentrated to remove CH3CN. The aqueous layer is extracted with methylene chloride (×4) and the organic layers are washed with brine, dried over MgSO4, filtered and concentrated to give the title compound as a white solid.

Provenance & Evidence