Oxalyl chloride → HCID 9950389, compound

Participants

Reaction Steps

2-Methyl-2-(6,7,8,9-tetrahydro-dibenzofuran-3-sulfonylamino)-propionic acid (387 mg, 1.15 mmol) was suspended in 1,2-dichloroethane (22 mL), then oxalyl chloride (438 mg, 3.45 mmol) was added dropwise. N,N-dimethylformamide (2 drops) was added and a gas evolved from the solution. The reaction was stirred until the solids were dissolved. The reaction mixture was concentrated by evaporation, washed with hexane, concentrated again, and dissolved in tetrahydrofuran (20 mL), then added to an aqueous tetrahydrofuran solution (1:1, 34 mL, 5° C.) of hydroxylamine hydrochloride (800 mg, 11.5 mmol) and sodium bicarbonate (1.8 g, 17.25 mmol). The reaction was stirred, warming up to room temperature, overnight. The tetrahydrofuran was removed from the reaction mixture in vacuo. To the residue, 1 M HCl and dichloromethane were added. The organic phase was separated from the organic phase, dried (over MgSO4), and concentrated. The crystals were rinsed with ethyl acetate, then collected by filtration to give N-hydroxy-2-methyl-2-(6,7,8,9-tetrahydro-dibenzofuran-3-sulfonylamino)-propionamide (a compound of general Formula IX) (235 mg, 58%), the structure of which is shown below. The melting point of this compound was determined to be 175-176° C. 1HNMR (CDCl3): δ10.0 (s, 1H), 7.6 (s, 1H), 7.4 (d, 1H), 7.2 (m, 2H), 2.6 (m, 2H), 2.4 (m, 2H) 1.6 (m, 4H), 1.0 (s, 6H) ppm.

Provenance & Evidence