Dimethyl Sulfoxide → HCID 58056620, compound

Participants

Reaction Steps

In a 10 mL round-bottomed flask, oxalyl chloride (46.1 mg, 31.8 μl, 356 μmol) was combined with DCM (5 mL) to give a colorless solution. DMSO (27.8 mg, 25.3 μl, 356 μmol) was added drop wise at −78° C. The reaction was stirred for 15 min. A solution of 8-(2-chlorophenylsulfonyl)-6-hydroxy-2-(4-(trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decan-1-one (124 mg, 246 μmol) in DCM (1 mL) was added. The reaction mixture was stirred for 30 min at −40° C. Triethylamine (74.6 mg, 103 μl, 737 μmol) was added drop wise and the reaction mixture was heated to r.t. and stirred for 3 h. The reaction mixture was poured into 15 mL DCM and washed with H2O (2×10 mL).The organic layers were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by flash chromatography (0 to 100% AcOEt in heptane) to afford the title compound as an off-white solid (73 mg, 59%). MS (ESI): 503.1 (MH+).

Provenance & Evidence