Sodium Methoxide → Methyl 3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)benzoate

Participants

Reaction Steps

Methyl 4-[1-(aminosulfonyl)-3-methoxy-3-oxopropyl]-3-bromobenzoate (187 mg, 0.492 mmol) in methanol (16 mL) was treated with sodium methoxide (281 μL, 4.92 mmol) at 0° C. The solution stirred at room temperature for 3 h and 30 minutes. The reaction mixture was purified by preparative LCMS to afford product as a white solid (66 mg, 38%). 1H NMR (400 MHz, CD3OD): δ 8.31 (d, J=1.8 Hz, 1H), 8.07 (dd, J=8.2, 1.8 Hz, 1H), 7.67 (d, J=8.2 Hz, 1H), 5.71 (dd, J=8.7, 6.7 Hz, 1H), 3.94 (s, 3H), 3.52 (dd, J=17.5, 8.6 Hz, 1H), 3.27 (m, 1H). LCMS found for C11H10BrNO5SNa (M+Na)30: m/z=370, 372.

Provenance & Evidence