Triethylamine → HCID 20088231, compound

Participants

Reaction Steps

To a solution of N-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]oxamic acid (651 mg, 2.12 mmol) in methylene chloride (5 mL) containing 2 drops of dimethylformamide at 0° C. under an argon atmosphere was added oxalyl chloride (0.39 mL, 4.45 mmol) and the resulting mixture was stirred for 1 h. This was added to a solution of hydroxylamine hydrochloride (591 mg, 8.50 mmol) and triethylamine (1.75 mL, 12.70 mmol) in 1:5 water/tetrahydrofuran (10 mL) at 0° C. under an argon atmosphere. The reaction mixture was stirred at 0° C. for 1 hour then allowed to warm to room temperature and stirred an additional 2 h. The mixture was partitioned between water and methylene chloride and the organic extract was dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 1:5:94 acetic acid/methanol/methylene chloride, to provide the hydroxy oxamide (489 mg, 72% ): m.p. 136°-137° C.

Provenance & Evidence