Compound 23
8-methyl-4H-thieno[3,2-c]thiochromene-2-carboxylate 5,5-dioxide
From: A small molecule interacts with VDAC2 to block mouse BAK-driven apoptosis
View in PubChem | MDL Molfile | Chemdraw file
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Ethyl 8-methyl-4H-thieno[3,2-c]thiochromene-2-carboxylate 22 (1.94 g, 6.68 mmol) was dissolved in DCM (15 mL) and cooled to 0 °C, portionwise m-chloroperoxybenzoic acid (2.99 g, 13.35 mmol) was added, the reaction was warmed up to room temperature and left stirring overnight. The reaction mixture was extracted with saturated sodium hydrogen carbonate three times and the product was purified using column chromatography. The product was eluted out at 40 % ethyl acetate/cyclohexane to give 23 (1.93 g, 5.99 mmol, 90 %) as a yellow solid. 1H-NMR (300 MHz, CDCl3): δ 1.37 (t, J = 7.1 Hz, 3H), 2.48 (s, 3H), 4.34 (q, J = 7.1 Hz, 2H), 4.42 (s, 2H), 7.34 (d, J = 5.7 Hz, 1H), 7.45 (s, 1H), 7.67 (s, 1H), 7.92 (d, J = 8.0 Hz, 1H). LCMS (ES+), m/z = 323.40 [M+H]+.
