Oxalyl chloride → HCID 10202316, compound

Participants

Reaction Steps

A dichloromethane solution of the acid synthesized in Example 1 (0.26 g, 0.64 mmol/10 mL CH2Cl2) was reacted with oxalyl chloride (0.1 mL, 0.77 mmol) and a catalytic amount of N,N-dimethylformamide under an atmosphere of nitrogen. After stirring at room temperature for 30 minutes, the solution was concentrated in vacuo. The crude acid chloride was dissolved in tetrahydrofuran and added to a tetrahydrofuran (60 mL)/water (20 mL) solution containing hydroxylamine hydrochloride (0.44 g, 6.4 mmol) and sodium bicarbonate (0.81 g, 9.6 mmol). The reaction mixture was stirred at room temperature overnight, then concentrated in vacuo. The crude product was diluted with ethyl acetate and washed with water, brine, dried (MgSO4), and concentrated. The resulting residue was recrystallized from hexane/ethyl acetate to give 0.14 g of the title compound.

Provenance & Evidence