Dimethyl Sulfoxide → HCID 21907578, compound

Participants

Reaction Steps

Dry DMSO (71 μL, 1.0 mmol, 2.0 eq) was added dropwise to a solution of oxalyl chloride (66 μL, 0.75 mmol, 1.5 eq) in CH2Cl2 (1 mL) at −78° C. After stirring for ten minutes, a solution of compound 1 (136 μL, 0.5 mmol) in CH2Cl2 (4 mL) was added dropwise, and the reaction was stirred for an additional thirty minutes at −78° C. before the addition of TEA (2.79 μL, 2.0 mmol, 4.0 eq). The reaction mixture was then allowed to warn slowly to 0° C., diluted with saturated NH4Cl, and extracted twice with Et2O. The combined organic phases were washed with water and brine, dried with Na2SO4, concentrated, and purified by column chromatography using a gradient of 50:50:EtOAc:Hexane to 100% EtOAc to give a white solid (46 mg, 32%): mp 158-159° C. 1HNMR (CDCl3, δ TMS): 0.50 (t, 3H), 1.25 (t, 3H), 1.50 (m, 1H), 1.82 (m, 1H), 2.04 (m, 1H), 2.17 (m, 1H), 2.33 (m, 1H), 2.58 (q, 2H), 2.88 (m, 2H), 3.77 (m, 1H), 3.91 (m, 1H), 4.19 (q, 1H), 4.33 (m, 1H), 7.02-7.15 (m, 3H, Ar—H), 7.66 (br, 1H, NH). MS−: m/z 288 ([M−H]−). Anal. (C17H23NO3): C, H, N.

Provenance & Evidence