Dimethyl Ether → 1-[2-N-[2-(trimethylsilyl)ethoxycarbonyl]pteroyl]-imidazole

Participants

Reaction Steps

To a mixture of 3.0 g of pteroic acid and 5.35 mL of triethylamine (TEA), 6.24 g of CDI as dissolved in 50 mL of DMSO was added and reacted at room temperature for 3.5 hours. To the reaction solution 2-(trimethylsilyl)ethanol (9.63 mL) was added, followed by further 5 hours' reaction at room temperature. The reaction solution was added dropwise into water (10 mL)-acetic acid (0.32 mL) and dimethyl ether (6.4 mL), vigorously stirred for a few minutes, and recovered as solid by suction filtration. The solid product was purified by column chromatography (silica gel column: eluent; 10% methanol in chloroform) and dried under reduced pressure to finally give 2.67 g (yield=54.8%) of aimed compound.

Provenance & Evidence