Hydrochloric Acid → HCID 57771365, compound

Participants

Reaction Steps

To a solution of (3S)-3-[4-((2S,5R)-2-acetoxy-spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester (107 mg) obtained in Step 1 in a mixed solvent of methanol (0.65 mL)-tetrahydrofuran (0.65 mL) was added 2N aqueous sodium hydroxide solution (0.28 mL) under ice-cooling, followed by stirring the mixture at room temperature overnight. To the reaction mixture was added 2N aqueous hydrochloric acid solution (0.28 mL), followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by thin-layer column chromatography on silica gel (acetic acid: methanol:chloroform (volume ratio)=0.1:1:20) to give (3S)-3-[4-((2S,5R)-2-hydroxy-spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid (79 mg). Configuration of the structure was determined by NMR spectrum (NOESY, HSQC).

Provenance & Evidence