Sodium Hydroxide → (R)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid

HRID 1247440Notes

Reaction equation

HRID 1247440 reaction equation
C([O:3][C:4](=[O:18])[C@H:5]([O:15][CH2:16][CH3:17])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[F:14])C.[OH-].[Na+]>[Na+].[Cl-].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[CH2:16]([O:15][C@H:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[F:14])[C:4]([OH:18])=[O:3])[CH3:17]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69290013(R)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid ethyl ester

Product 1

HCID 69290932(R)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acidYield 82.1%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 24243Trisodium PhosphateSolvent

Procedure

An emulsion of (R)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid ethyl ester (416 mg) in 0.1M NaCl, 3 mM Natriumphosphat buffer pH 7.0 (75 ml) was cooled to 4–5° C. was treated with hog liver esterase suspension (0.175 ml). The reaction mixture was stirred for 4 days while maintaining the pH at 7 by gradual addition of 0.1N NaOH (totally 12.8 ml). The reaction mixture was washed with CH2Cl2, then brought to pH 2 by the addition of 2N HCl and extracted with EtOAc. The EtOAc layer was dried over Na2SO4, filtrated and concentrated to give (R)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid (304 mg, 97.1% ee) as yellow semisolid.

Workup

  1. temperaturewhile maintaining the pH at 7
  2. washThe reaction mixture was washed with CH2Cl2
  3. additionbrought to pH 2 by the addition of 2N HCl
  4. extractionextracted with EtOAc
  5. dry with materialThe EtOAc layer was dried over Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-44e46a73abea47dc8f0f74558ae7b609
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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