Hydrochloric Acid → HCID 19046358, compound

HRID 1781560Notes

Reaction equation

HRID 1781560 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14]S(C2C=CC(C)=CC=2)(=O)=O)[C:4]=1[CH2:25][C:26]1[CH2:30][CH2:29][C:28]([CH2:32][C:33]([OH:35])=[O:34])(C)[CH:27]=1.O.[OH-].[Li+].Cl.[CH3:40]O>O.C(OCC)(=O)C>[OH:14][C:5]1[C:4]([CH2:25][C:26]2[CH2:30][CH2:29][CH:28]([CH2:32][C:33]([OH:35])=[O:34])[C:27]=2[CH3:40])=[C:3]([O:2][CH3:1])[C:11]([CH3:12])=[C:10]2[C:6]=1[C:7](=[O:13])[O:8][CH2:9]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 19046404HCID 19046404, compound

Product 1

HCID 19046358HCID 19046358, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy -5-isobenzofuranylmethyl)-1-methylcyclopent-2-en-1-ylacetic acid obtained in Example ZC-1G was dissolved in a mixture of methanol (8 mL) and water (2 mL) and treated with lithium hydroxide monohydrate (0.15 g). After 4 hours, the reaction was diluted with ethyl acetate and made acidic with 5% hydrochloric acid. After two extractions with ethyl acetate, the product was washed out of the combined organic layers with 2M NaOH. Acidification of the basic layers with 5% hydrochloric acid and extraction of the product into ethyl acetate was followed by drying the organic layer with magnesium sulfate. Filtration and solvent removal was followed by two flash chromatographies (hexanes/ethyl acetate, 4/1 with 1% HOAc; then methylene chloride/methanol 25/1) to provide 3-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-ylacetic acid (0.010 g) m.p. 153°-159° C.

Workup

  1. extractionAfter two extractions with ethyl acetate
  2. washthe product was washed out of the combined organic layers with 2M NaOH
  3. extractionAcidification of the basic layers with 5% hydrochloric acid and extraction of the product into ethyl acetate
  4. dry with materialby drying the organic layer with magnesium sulfate
  5. filtrationFiltration and solvent removal

Sources & evidence

ORD record
ord-d044b48c5b3d413691e992c6ba016b16
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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