Hydrochloric Acid → HCID 22262119, compound

HRID 1610379Notes

Reaction equation

HRID 1610379 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:26])[CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)[C:10]([O:12]CC)=[O:11].[Na].[OH-].Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:26])[CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=1)[C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 961HydroxideHCID 5360545SodiumHCID 86593242HCID 86593242, compound

Product 1

HCID 22262119HCID 22262119, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-3-(2-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate (15.7 g, 42.5 mmol) in methanol (100 ml) was added 2N aqueous sodium, hydroxide solution (43 ml, 86 mmol) and the mixture was stirred overnight at room temperature. The reaction solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give (2RS,3RS)-3-(2-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (11.7 g, 80%).

Workup

  1. extractionextracted with ethyl acetate (200 ml×2)
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a5a19ccb03d4425594ede935bb0e13ac
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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