Diisopropylethylamine → Ethyl 4-([2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-amino)-butanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 180 mg of ethyl 4-[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethylamino]-butanoate in 18 ml of acetonitrile was added 207 mg of 1-iodo-2-[2-(2-methoxy-ethoxy)-ethoxy]-ethane and 192 μl of diisopropylethylamine. The mixture was heated for 3 days at 80° C. and then concentrated under reduced pressure and purified by flash chromatography on silica (Merck SuperVarioFlash 15 g column, Si60 15-40 μm), using a DCM/MeOH/water mixture (40/5/0.5). The fractions containing the desired product were combined and concentrated under reduced pressure. 51 mg of ethyl 4-([2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-amino)-butanoate were obtained. LC/MS (B): tr=0.70 min; [M+H]+: m/z 459.

Provenance & Evidence