Hydrochloric Acid → HCID 22261852, compound

HRID 1610567Notes

Reaction equation

HRID 1610567 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]([OH:36])[CH:16]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:35])([F:34])[CH:31]([F:33])[F:32])[CH:24]=2)[C:17]([O:19]CC)=[O:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]([OH:36])[CH:16]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:34])([F:35])[CH:31]([F:32])[F:33])[CH:24]=2)[C:17]([OH:19])=[O:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86593265HCID 86593265, compound

Product 1

HCID 22261852HCID 22261852, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-3-[3-(benzyloxy)phenyl]-3-hydroxy-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate (10.7 g, 21.2 mmol, crude) in methanol (50 ml) was added. 2N aqueous sodium hydroxide solution (21 ml, 42 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate (50 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The obtained crude crystals were washed with hexane to give the objective substance (7.90 g, 49% in 3 steps).

Workup

  1. extractionextracted with ethyl acetate (50 ml×2)
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. customevaporated under reduced pressure
  5. customThe obtained crude crystals
  6. washwere washed with hexane
  7. customto give the objective substance (7.90 g, 49% in 3 steps)

Sources & evidence

ORD record
ord-68affd04733e499582b682c8b4eea030
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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