Trifluoroacetic acid → HCID 68620201, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-[1-(2-fluoro-4-iodo-phenylcarbamoyl)-2-pyridin-2-yl-ethyl]-carbamic acid tert-butyl ester (1.2 g, 2.47 mmol) in dichloromethane (5 mL) at 0° C. was added trifluoroacetic acid (5 mL) and the mixture stirred at 0° C. for 1 hour. The reaction mixture was concentrated in vacuo and the residue suspended in ice cold water. The aqueous suspension was neutralized with saturated aqueous sodium carbonate solution to basic then extracted with dichloromethane (three times). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography over silica gel gradient eluted from 100% hexane up to 100% ethyl acetate in 40 minutes. Concentration of the product containing fractions gave (S)-2-amino-N-(2-fluoro-4-iodo-phenyl)-3-pyridin-2-yl-propionamide as a yellow solid (806 mg, 85%).

Provenance & Evidence