(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 617377Notes

Reaction equation

HRID 617377 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-b69a9106953d429aa541abf79f28d33a
Source dataset
uspto-grants-1999_09
Patent number
US05948792

Reaction notes

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