(2R,5R)-2-(t-butyl)-5-((1R)-3-oxocyclopentyl)-5-phenyl-1,3-dioxolan-4-one → (2R)-[(1R)-3-oxocyclopentyl]-2-hydroxy-2-phenylacetic acid

HRID 1637373Notes

Reaction equation

HRID 1637373 reaction equation
C([C@H]1[O:9][C:8](=[O:10])[C@@:7]([C@@H:17]2[CH2:21][CH2:20][C:19](=[O:22])[CH2:18]2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6]1)(C)(C)C>CO.[OH-].[Na+]>[O:22]=[C:19]1[CH2:20][CH2:21][C@@H:17]([C@@:7]([OH:6])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]([OH:10])=[O:9])[CH2:18]1

Participants

4

Reactant 1

HCID 11174148(2R,5R)-2-(t-butyl)-5-((1R)-3-oxocyclopentyl)-5-phenyl-1,3-dioxolan-4-one

Product 1

HCID 54364298(2R)-[(1R)-3-oxocyclopentyl]-2-hydroxy-2-phenylacetic acidYield 101.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 61 mg of (2R,5R)-2-(t-butyl)-5-[(1R)-3-oxocyclopentyl]-5-phenyl-1,3-dioxolan-4-one in 3 ml of methanol, 1 ml of 1N aqueous sodium hydroxide solution was added, followed by stirring for 3 hours at room temperature. Distilling the methanol off under reduced pressure, the residue was diluted with water and washed with diethyl ether. The aqueous layer was made acidic with 1N hydrochloric acid and extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate to provide 48 mg of the title compound.

Workup

  1. distillationDistilling the methanol off under reduced pressure
  2. additionthe residue was diluted with water
  3. washwashed with diethyl ether
  4. extractionextracted with diethyl ether
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-c138e93dea71405c80879d479d59213f
Source dataset
uspto-grants-2000_03
Patent number
US06040449

Reaction notes

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