Hydrochloric Acid → HCID 22261453, compound

HRID 1610645Notes

Reaction equation

HRID 1610645 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]([O:22][CH:23]([CH3:25])[CH3:24])[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]([O:22][CH:23]([CH3:24])[CH3:25])[CH:17]=2)[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86593286ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-[3-(isopropyloxy)benzyl]propanoate

Product 1

HCID 22261453HCID 22261453, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution-of ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-[3-(isopropyloxy)benzyl]propanoate (9.8 g, 27.2 mmol) in methanol (50 ml) was added 2N aqueous sodium hydroxide solution (27.2 ml, 54.4 mmol), and the mixture was stirred at room temperature for 3 hrs. The reaction solution was acidified with 6N hydrochloric acid (100 ml). The mixture was extracted with ethyl acetate (200, 100 ml). The extract was washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was crystallized from hexane to give the objective substance (7.44 g, 82%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (200, 100 ml)
  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 hexane
  6. customto give the objective substance (7.44 g, 82%)

Sources & evidence

ORD record
ord-fd955ff3dd2243b3a3450f076687f55d
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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