Pyridine → HCID 70178435, compound

Participants

Reaction Conditions

Reaction Steps

(S)-Ethyl-2-tert-butyloxycarbonylamino-3-(4-aminophenyl)propionate (0.103 g, 0.33 mmol) was dissolved in CH2Cl2 (1 mL) in a two-necked flask fitted with a thermometer and nitrogen line. The flask was cooled to 0° C. and pyridine (1.1 eq, 0.36 mmol, 0.030 mL) was added via syringe. Methanesulfonyl chloride (1.1 eq, 0.36 mmol, 0.028 mL) was then added dropwise at such a rate as to maintain the temperature <10° C. After addition was complete, the ice bath was removed and the bright yellow solution was allowed to warm to room temperature, turning bright orange and then pink in color as it stirred over the next two hours. The solution was poured into 1 M aqueous CuSO4 and the organic portion was separated. It was washed once again with aqueous CuSO4, then dried over MgSO4, filtered, and concentrated to a colorless oil (0.11 g, 84%).

Provenance & Evidence