Sodium Hydroxide → (2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetic acid

HRID 369906Notes

Reaction equation

HRID 369906 reaction equation
C([C@H]1[O:9][C:8](=[O:10])[C@@:7]([C@@H:17]2[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6]1)(C)(C)C.[OH-].[Na+]>CO>[F:22][C:19]1([F:23])[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 2

HCID 14798Sodium HydroxideHCID 10592061(2R,5R)-2-(t-butyl)-5-((1R)-3,3-difluorocyclopentyl)-5-phenyl-1,3-dioxolan-4-One

Product 1

HCID 10890505(2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetic acidYield 87.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.4 g of (2R,5R)-2-(t-butyl)-5-((1R)-3,3-difluorocyclopentyl)-5-phenyl-1,3-dioxolan-4-one in 30 ml of methanol, 10 ml of a 1N aqueous solution of sodium hydroxide was added, followed by stirring for 3 hours at room temperature. After distilling the methanol off under reduced pressure, the reaction mixture was diluted with water, and washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with diethyl ether, while the organic layer was dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure gave 1.66 g of the title compound.

Workup

  1. distillationAfter distilling the methanol off under reduced pressure
  2. additionthe reaction mixture was diluted with water
  3. washwashed with diethyl ether
  4. extractionextracted with diethyl ether, while the organic layer
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-167a143824cd40eca968853384db051f
Source dataset
uspto-grants-2000_10
Patent number
US06140333

Reaction notes

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