Acetic Acid → HCID 10178734, compound

Participants

Reaction Conditions

Reaction Steps

Glacial acetic acid (130 ml) was added to 500 ml of a THF solution containing a mixture of diethyl β-(4-t-butyldimethylsilyloxy-3-methoxy-5-methylphenyl)-β-[N-(3-pyridyl)-amino]-ethylphosphonate (90.5 g, 0.18 mol) and tetrabutylammonium fluoride trihydrate (TBAF) (224.5 g, 0.71 mol). After stirring at 20° C. for 3 h a GLC test showed that the Tbs protected compound has entirely reacted. The reaction mixture was extracted with dichloromethane, the organic phase was washed with a saturated bicarbonate solution, dried over MgSO4 and evaporated. Purification by column chromatography (silica gel, 9/1 CH2Cl2/MeOH) gave 53 g of pure fractions. Recrystallization from a mixture of petroleum ether/CH2Cl2 gave 27 g (39%) of the title compound as a white solid, mp=156-158° C.

Provenance & Evidence