5-Chloro-1H-indole-2-carboxylic acid → (+/-)-[(5-Chloro-1h-indole-2-carbonyl)-amino]-3-hydroxy-propionic acid methyl ester

Participants

Reaction Steps

D,L-Serine methyl ester hydrochloride (2.1 mmol) and 5-chloro-1H-indole-2-carboxylic acid (2.0 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, washed with acid first then with saturated NaHCO3) and the product purified by chromatography on silica gel eluted with 10, 20, 40 and 60% ethyl acetate in hexanes: Yield 565 mg, 95%; HPLC (60/40) 3.46 minutes (98%); mp 153-155 ° C.; TSPMS 297/299 (MH+, 100/40%);

Provenance & Evidence