Sulfuric Acid → HCID 131717759, compound

Participants

Reaction Steps

90 mg of (±)-(5RS)-5-acetoxy-5-[cis-(2RS)-2-((1E,3E)-(5RS)-5-tert-butyldiphenylsilyloxy-trideca-1,3-dien-7-inyl)-(1RS)-cyclohex- 1-yl]-pentanoic acid (produced in example 59) is stirred together with 1.8 ml of ethanolic potassium hydroxide solution (5 g of potassium hydroxide in 62.5 ml of water and 187.5 ml of ethanol) for 4 days at 24° C. Then, it is acidified with 10% sulfuric acid to pH 5, extracted several times with ethyl acetate, the organic phase is washed with brine, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with hexane/10-70% of ethyl acetate. 32 mg of (±)-(5RS)-5-acetoxy-5-[cis-(2RS)-2-((1E,3E)-(5RS)-5-hydroxy-trideca-1,3-dien-7-inyl)-(1RS)-cyclohex-1-yl]-pentanoic acid is obtained.

Provenance & Evidence