Hexamethyldisilazane → HCID 18626641, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid (300 mg, 0.88 mmol) and 1 drop of N,N-dimethylformamide in methylene chloride (2 mL) was cooled to 0° C. and then slowly treated with oxalyl chloride (84 μL, 0.97 mmol). The reaction mixture was stirred at 0° C. for 10 min and then stirred at 25° C. for 1 h. The resulting reaction mixture was then treated dropwise with 1,1,1,3,3,3-hexamethyldisilazane (560 μL, 2.64 mmol) and subsequently stirred at 25° C. for 15 h. The resulting reaction mixture was diluted with methylene chloride (20 mL) and methanol (15 mL) and then washed with a 5% aqueous sulfuric acid solution (20 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/3 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionamide (140 mg, 47%) as a yellow foam: mp 72-76° C. (foam to gel); FAB-HRMS m/e calcd for C15H20N2O5S (M+H)+341.1172, found 341.1181.

Provenance & Evidence