Water → (Z)-7-{(1R,2S,3R)-3-Hydroxy-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

HRID 9242Notes

Reaction equation

HRID 9242 reaction equation
[CH3:1][O:2][C:3](=[O:43])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]1[C:14](=[O:15])[CH2:13][C@@H:12]([O:16][Si](C(C)(C)C)(C)C)[C@@H:11]1[C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[CH:29]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[CH2:28][CH2:27]2.O.C1COCC1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:43])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]1[C:14](=[O:15])[CH2:13][C@@H:12]([OH:16])[C@@H:11]1[C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[CH:29]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[CH2:28][CH2:27]2

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 69367144(Z)-7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

Product 1

HCID 69595718(Z)-7-{(1R,2S,3R)-3-Hydroxy-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl esterYield 69.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 15-4 (20 mg, 0.032 mmol) in acetic acid (0.3 mL)/water (0.1 mL)/THF (0.1 mL) was stirred at room temperature. After two days, saturated NaHCO3 solution was added and the resulting mixture was extracted with dichloromethane (3×20 mL). The combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexanes→30% →40%) which gave the title compound (11 mg, 67%).

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane (3×20 mL)
  2. dry with materialThe combined dichloromethane solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexanes→30% →40%) which

Sources & evidence

ORD record
ord-37fac7bdf06c46dc8609a5f9d997917f
Source dataset
uspto-grants-2006_08
Patent number
US07091231B2

Reaction notes

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