Oxalyl chloride → HCID 178501142, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (500 mg, 2.69 mmol) in dichloromethane (3 mL) at 0° C. was added oxalyl chloride (0.26 mL, 2.95 mmol) dropwise. The solution was stirred at 0° C. for 30 min and then allowed to warm to room temperature and stirred for one hour. The solution was then cooled back to 0° C. and 2-(trimethylsilyl)-1,3-thiazole (0.63 mL, 4.03 mmol) was added. The solution was allowed to warm to room temperature and then stirred for one hour. The solution was then poured into cold saturated sodium bicarbonate and then diluted with dichlormethane. The organic phase was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-30% ethyl acetate/hexanes) to provide methyl trans-4-(1,3-thiazol-2-ylcarbonyl)cyclohexanecarboxylate. MS ESI calc'd. for C12H16NO3S [M+H]+ 254. found 254. 1H NMR (500 MHz, CDCl3) δ 8.01 (dd, J=1.6, 2.9 Hz, 1H), 7.67 (dd, J=1.7, 2.9 Hz, 1H), 3.77-3.67 (m, 3H), 3.62 (t, J=11.1 Hz, 1H), 2.35 (t, J=10.4 Hz, 1H), 2.18-2.06 (m, 4H), 1.68-1.48 (m, 4H).

Provenance & Evidence