Sodium Hydroxide → HCID 22261428, compound

HRID 1610653Notes

Reaction equation

HRID 1610653 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][CH:27]=1)[CH2:9][CH:10]([CH:16]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[OH:17])[C:11]([O:13]CC)=[O:12])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].S([O-])(O)(=O)=O.[K+]>CO>[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][CH:27]=1)[CH2:9][CH:10]([CH:16]([C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)[OH:17])[C:11]([OH:13])=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 86593287HCID 86593287, compound

Product 1

HCID 22261428HCID 22261428, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-2-[3-(tert-butyloxy)benzyl]-3-(4-fluorophenyl)-3-hydroxypropanoate (8.8 g, 23.5 mmol) in methanol (100 ml) was added 2N aqueous sodium hydroxide solution (23.5 ml, 47 mmol), and the mixture was stirred at room temperature for 3 hrs. The reaction solution was acidified with 5% aqueous potassium hydrogen sulfate solution (100 ml). The mixture was extracted with ethyl acetate (200 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 (2RS,3RS)-2-[3-(tert-butyloxy)benzyl]-3-(4-fluorophenyl)-3-hydroxypropanoic acid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (200 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

Sources & evidence

ORD record
ord-9f5a961283574ef3859708c759c8a19e
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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