Dimethyl Sulfoxide → HCID 118061731, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (0.549 mL, 6.27 mmol) in DCM (15 mL) was added DMSO (0.890 mL, 12.54 mmol) as a solution in DCM (5 mL) slowly at −78° C. The resultant solution was stirred for 30 min prior to dropwise addition of Intermediate 258B (0.5 g, 3.14 mmol) as solution in DCM (5 mL). The resultant mixture was stirred for an additional 2 h at −78° C. TEA (4.37 mL, 31.4 mmol) was added to the reaction and the reaction mixture was allowed to stir at −78° C. for 30 min. The mixture was then warmed to RT and a saturated aqueous NH4Cl solution was added and extracted with dichloromethane (3×10 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate concentrated under reduced pressure. The crude product was purified by silica gel chromatography (12 g REDISEP® column, eluting with 30% EtOAc in hexane). Fractions containing the product were combined and evaporated to afford Intermediate 258C as a pale yellow liquid (0.12 g, 22%, mixture of cis and trans isomers). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.63 (d, J=1.51 Hz, 1H), 3.95-4.15 (m, 2H), 3.08-3.28 (m, 1H), 2.53-2.61 (m, 2H), 2.16-2.28 (m, 1H), 1.93-2.14 (m, 2H), 1.37-1.43 (s, 1H), 1.21-1.30 (s, 2H), 1.13-1.21 (m, 3H).

Provenance & Evidence