Dimethyl Sulfoxide → HCID 68294584, compound

Participants

Reaction Steps

Powdered KOH (1525 mg, 27.19 mmol) was added to DMSO (3 mL) and the resulting mixture was stirred for 5 min at RT. To this solution was added 100 (902 mg, 2.719 mmol) followed immediately by iodomethane (1.35 mL, 21.75 mmol). The resulting mixture was stirred at RT for 5 h. The reaction mixture was diluted with EtOAc and washed sequentially with H2O, 2M HCl and brine. The organic layer was dried, filtered, and concentrated. The crude product was purified by SiO2 chromatography eluting with 10:1 DCM/EtOAc. The impure product therefrom was rechromatographed under similar conditions to afford 586 mg (59.90%) of (S)-methyl 4-(tert-butoxycarbonyl(methyl)amino)-3-(4-chloro-3-fluorophenyl)butanoate (102).

Provenance & Evidence