Ethanol → HCID 69084129, compound

Participants

Reaction Steps

A solution of 1-((3aR,5S,6S,7R,7aR)-2-(dimethylamino)-6,7-bis(4-methoxybenzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)ethanone (280 mg, 0.56 mmol) in dichloromethane (10 mL) was treated with (diethylamino)sulfur trifluoride (451 g, 2.80 mol) and ethanol (5.2 mg, 0.11 mmol) overnight at room temperature. The reaction was then quenched by addition of sat. aqueous sodium carbonate solution (50 mL), and extracted with dichloromethane (3×20 mL). The combined organic layers were dried over anhydrous magnesium sulfate and condensed under vacuum to give a crude product 55 (140 mg), which was used in the next step without further purification. (ES, m/z) [M+H]+ 523.0; 1H NMR (300 MHz, CD3Cl) δ 1H NMR (300 MHz, CDCl3) δ 7.24-7.30 (m, 4H), 6.84-6.95 (m, 4H), 6.30-6.32 (m, 1H), 4.57-4.62 (m, 4H), 4.27-4.35 (m, 2H), 3.81-3.91 (m, 8H), 2.99-3.01 (m, 6H), 1.56-1.62 (m, 3H).

Provenance & Evidence