Dimethyl Sulfoxide → HCID 58746799, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (74.3 μL, 0.878 mmol) was stirred in methylene chloride (2.6 mL), and the resulting solution was cooled to −78° C., whereupon dimethyl sulfoxide (142 μL, 2.00 mmol) was added. Then to the mixture, a solution of 2-tert-butyl-5-(4-[2-(hydroxymethyl)-5-oxopyrrolidin-2-yl]methylphenyl)isothiazolidin-3-one 1,1-dioxide (105 mg, 0.266 mmol) in dichloromethane (2.0 mL) was added dropwise, within five minutes. The mixture was stirred for fifteen minutes at −78° C.; after addition of N,N-diisopropylethylamine (695 μL, 3.99 mmol) the mixture was allowed to reach room temperature, and poured into water (1 mL). The aqueous phase was extracted twice with dichloromethane (5 mL) and the combined extracts were evaporated to give the crude aldehyde as a yellow oil. Purification on the preparative LCMS gave the desired aldehyde as a tan solid (30 mg, 30%). 1H NMR (400 MHz, CDCl3): δ 9.60 (s, 1H), 7.38 (m, 2H), 7.25 (m, 2H), 6.70 (s, 1H), 4.76 (m, 1H), 3.17 (m, 1H), 2.92 (m, 1H), 2.30 (m, 2H), 2.18 (m, 2H), 1.65 (s, 9H); LCMS found for C19H25N2O5S (M+H)+: m/z=393

Provenance & Evidence