Oxalyl chloride → HCID 69642585, compound

Participants

Reaction Steps

A solution of acetic acid 2-[acetyl-(1H-indol-7-ylmethyl)-amino]-ethyl ester (4.76 g, 17.36 mmol) in CH2Cl2 (100 ml) was cooled to 0° C. Oxalyl chloride (3.27 g, 26.04 mmol) was added and the reaction was warmed to room temperature. Upon completion, the reaction was cooled to −78° C. and sodium methoxide (4.14 mmol, 18.1 mmol, 25% w/v in methanol) was added. The solution was warmed to 20–24° C., and the mixture was diluted with ethyl acetate (400 mL), washed with saturated aqueous NaHCO3, brine, dried (MgSO4), filtered, and concentrated. SiO2 chromatography afforded the title compound (1.12 g, 20%) and (7-{[(2-Acetoxy-ethyl)-acetyl-amino]-methyl}-1H-indol-3-yl)-oxo-acetic acid methyl ester (3.0 g, 48%). MS (electrospray, m/z) 319.2 (M++1), 317.2 (M−−1).

Provenance & Evidence