Hydroxyphenylacetic acid → Methyl 4-(7,12-dihydroxy-3-{2-[2-(4-hydroxyphenyl)acetylamino]ethoxy}-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl)pentanoate

Participants

Reaction Conditions

Reaction Steps

700 mg of methyl 4-[3-(2-aminoethoxy)-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl]pentanoate, 230 mg of 4-hydroxyphenylacetic acid and 305 mg of HOBT are dissolved in 10 ml of THF and a solution of 342 mg of DCC in 10 ml of THF is injected at 0° C. The mixture is stirred at 0° C. for one hour and then at RT for 25 hours. The precipitate is filtered off, the filtrate is diluted with 150 ml of a 10% aqueous NaHCO3 solution and the mixture is extracted three times with 100 ml of EA each time. The extract is dried over Na2SO4 and the solvent is removed in vacuo. Chromatography on silica gel using EA/MeOH 10:1 yields 660 mg of a colorless oil.

Provenance & Evidence