Hydrochloric Acid → (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(3-trifluoromethylbenzyl)propionic acid

HRID 1610269Notes

Reaction equation

HRID 1610269 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:26])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:26])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=2)[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86593223ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(3-trifluoromethylbenzyl)propionate

Product 1

HCID 22261726(2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(3-trifluoromethylbenzyl)propionic acidYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(3-trifluoromethylbenzyl)propionate (7.9 g, 21.3 mmol) in methanol (50 ml) was added 1N aqueous sodium hydroxide solution (42.7 ml, 42.7 mmol) and the mixture was stirred at room temperature for 3 hrs. The reaction solution was acidified with 1N hydrochloric acid (100 ml) and extracted with ethyl acetate (200 ml×2). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was crystallized from a mixture of hexane and diethyl ether to give (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(3-trifluoromethylbenzyl)propionic acid (6.20 g, 85%).

Workup

  1. extractionextracted with ethyl acetate (200 ml×2)
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was crystallized from a mixture of hexane and diethyl ether

Sources & evidence

ORD record
ord-7fae9b16d85044f6983be28052605965
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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