Sulfuric Acid → HCID 131717759, compound
Reaction equation
[C:1]([O:4][CH:5]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]1/[CH:18]=[CH:19]/[CH:20]=[CH:21]/[CH:22]([O:31][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:23][C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])(=[O:3])[CH3:2].[OH-].[K+].S(=O)(=O)(O)O>>[C:1]([O:4][CH:5]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]1/[CH:18]=[CH:19]/[CH:20]=[CH:21]/[CH:22]([OH:31])[CH2:23][C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])(=[O:3])[CH3:2]Participants
Procedure
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.
Workup
- extractionextracted several times with ethyl acetate
- washthe organic phase is washed with brine
- customdried on sodium sulfate
- concentrationconcentrated by evaporation in a vacuum
- customThe residue is chromatographed on silica gel with hexane/10-70% of ethyl acetate
Sources & evidence
- ORD record
- ord-94935d06183342cd83b06b37bfa46914
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05187286
Reaction notes
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