Acetic Acid → HCID 58746678, compound

Participants

Reaction Steps

Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-chlorophenyl]propanoate (300 mg, 0.598 mmol) in tetrahydrofuran (6.00 mL) was cooled to 0° C. and treated with lithium tetrahydroborate solution in tetrahydrofuran (2.0 M, 0.329 mL). The reaction was allowed to stir for 0.5 h at rt. After addition of acetic acid (0.5 mL), the solution was diluted with ethyl acetate (100 mL), washed with water (100 mL), separated, dried over sodium sulfate, filtered and was concentrated in vacuo. The crude material was purified by silica gel chromatography (5–30% ethyl acetate/hexanes) to afford the product as a white solid (162 mg, 54%). 1H NMR (400 MHz, CD3OD): δ 7.45–7.42 (m, 2H), 7.31–7.27 (m, 1H), 5.59 (t, J=8.0 Hz, 1H), 4.39–4.36 (m, 1H), 3.70 (s, 3H), 3.38–3.33 (m, 1H), 3.25–3.14 (m, 2H), 2.95–2.92 (m, 1H), 1.67 (s, 9H), 1.37 (s, 9H); LCMS found for C17H24ClN2O5S (M+H)+: m/z=403.

Provenance & Evidence