Methanol → HCID 59822064, compound

Participants

Reaction Steps

0.9 g 17,17-difluoro-15beta-{3-[(5-methyl-1,3-thiazol-2-yl)amino]-3-oxopropyl}estra-1(10),2,4-triene-3-carboxylic acid methyl ester and 0.5 g LiOH are mixed with 30 ml MeOH, 50 ml THF and 30 ml H2O and stirred at 80° C. (water bath) for about 30 min. H2O is added, the reaction mixture is extracted with EtOAc three times. The combined aquatic layers are acidified with KHSO4aq to pH 2-3, and extracted the times with EtOAc. The latter organic layers are combined, washed with brine, dried (Na2SO4) and the solvent removed. 620 mg crude compound was obtained which was used in the following step without further purification. Purifying by column chromatography (CH2Cl2: MeOH:AcOH 37:3:0.1) give 77 mg of pure 17,17-difluoro-15beta-{3-[(5-methyl-1,3-thiazol-2-yl)amino]-3-oxopropyl}estra-1(10),2,4-triene-3-carboxylic acid (=EXAMPLE 9, NMR spectra see below).

Provenance & Evidence