Dichloromethane → HCID 58746441, compound

Participants

Reaction Steps

A solution of benzyl (1S)-1-(1H-benzimidazol-2-yl)-2-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-methylphenyl]ethylcarbamate acetate (956 mg, 1.65 mmol), [β-(trimethylsilyl)ethoxy]methyl chloride (731 μL, 4.13 mmol), N,N-diisopropylethylamine (1.73 mL, 9.91 mmol) and methylene chloride (30.0 mL) was stirred at 25° C. for 3 h. The reaction was diluted with 1 N HCl solution and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (0.82 g, 64%). 1H NMR (400 MHz, CD3OD): δ 7.79 (m, 1H), 7.68 (m, 1H), 7.4 (m, 8H), 7.11 (s, 1H), 5.5 (m, 4H), 5.1 (m, 4H), 3.75 (m, 2H), 3.55 (m, 2H), 3.3 (m, 4H), 2.52 (s, 1.5H), 2.40 (s, 1.5H), 1.02 (m, 2H), 0.94 (m, 2H), 0.11 (s, 9H), 0.01 (s, 9H); MF=C39H54N32O7SSi2; LCMS found for C39H55N4O7SSi2 (M+H)+: m/z=779.

Provenance & Evidence