Sodium Hydroxide → HCID 22261844, compound

HRID 1610613Notes

Reaction equation

HRID 1610613 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:27])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22][C:23]([F:26])([F:25])[F:24])[CH:17]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:27])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22][C:23]([F:24])([F:25])[F:26])[CH:17]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22262080HCID 22262080, compound

Product 1

HCID 22261844HCID 22261844, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-{3-[(trifluoromethyl)thio]benzyl}propanoate (5.30 g, 13.17 mmol) in methanol (150 ml) was added 2N aqueous sodium hydroxide solution (13.2 ml, 26.4 mmol), and the mixture was stirred overnight at room temperature. After the reaction solution was concentrated, 1N hydrochloric acid was added. The mixture was acidified and extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the objective substance (3.98 g, 81%).

Workup

  1. concentrationAfter the reaction solution was concentrated
  2. addition1N hydrochloric acid was added
  3. extractionextracted with ethyl acetate (200 ml×2)
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. customevaporated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate-hexane
  8. customto give the objective substance (3.98 g, 81%)

Sources & evidence

ORD record
ord-d5c6912165f74b07bbf6ecdd321b1cf1
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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