Dichloromethane → HCID 58946310, compound

Participants

Reaction Conditions

Reaction Steps

(2R)-1-Acetoxy-2-acetylamino-2-ethyl-4-{1-methyl-5-[4-(4-methylphenyl)-1-(4-(4-methylphenyl)butanoyloxy)but-1-enyl]pyrrol-2-yl}butane (372 mg, 0.620 mmol) obtained in Example 12 (12a) was dissolved in a mixture of tetrahydrofuran (5 mL) and methanol (5 mL), and water (5 mL) and lithium hydroxide monohydrate (260 mg, 6.20 mmol) were added thereto, followed by stirring of the mixture at 50° C. for 4 hours. After cooling, water was added to the reaction mixture and methylene chloride was added thereto to separate it. The thus obtained organic phase was separated, washed with a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by basic silica gel (NH type) chromatography (methylene chloride:methanol, 100:1) to obtain crude (2R)-2-amino-2-ethyl-4-{1-methyl-5-[4-(4-methylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol (206 mg). A 4N hydrochloric acid-dioxane solution (0.135 mL, 0.54 mmol) was added to a solution of the thus obtained crude product in methanol (5.0 mL) under ice-cooling and the mixture was stirred for 10 minutes. The mixture was concentrated under reduced pressure, ethyl acetate was added thereto and the precipitated crystal was collected by filtration. The crystal was washed with ethyl acetate and dried under reduced pressure to obtain the title compound (212 mg, yield: 88%).

Provenance & Evidence