Triethylamine → HCID 11960177, compound

Participants

Reaction Steps

To a stirred solution of 3-(2,6-Dimethylbenzyloxy)phenylacetic acid (Step C, 2.06 g, 7.6 mmol) in methylene chloride (20 ml) at 0° C., oxalyl chloride (1.49 g, 11.9 mmol) was added in a dropwise manner. The reaction mixture was stirred at room temperature for 2 hours. Simultaneously, in a separate flask, a mixture of hydroxylamine hydrochloride (2.98 g, 43 mmol) and triethylamine (10 ml) was stirred in THF/water (5:1, 45 ml) at 0° C. for 1-2 hours. At the end of 2 hours, the oxalyl chloride reaction mixture was concentrated and the yellow residue was dissolved in methylene chloride (10 ml). The mixture was added slowly to the hydroxylamine mixture at 0° C. The reaction mixture was stirred for 24 hours, and concentrated. The residue was taken into chloroform and washed with water, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol, 92.5:7.5 spiked with acetic acid) to give the title compound.

Provenance & Evidence