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

HRID 1247439Notes

Reaction equation

HRID 1247439 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH: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])[CH3:2].[OH-].[Na+]>[Na+].[Cl-].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[CH2:1]([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])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69290014(RS)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid ethyl ester

Product 1

HCID 69290013(R)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid ethyl esterYield 29.7%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 24243Trisodium PhosphateSolvent

Procedure

An emulsion of (RS)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid ethyl ester (1.11 g) in 0.1M NaCl, 3 mM Natriumphosphat buffer pH 7.0 (260 ml) was cooled to 4–5° C. and treated with lipase from Rhizomucor miehei. The reaction mixture was stirred for 4 days at 4–5° while maintaining the pH at 7 by gradual addition of 0.1N NaOH (totally 25.5 ml), then extracted with CH2Cl2 and then EtOAc. The organic layers were dried over Na2SO4, then concentrated to give (R)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid ethyl ester (330 mg, 98.9% ee).

Workup

  1. additiontreated with lipase from Rhizomucor miehei
  2. temperaturewhile maintaining the pH at 7
  3. extractionthen extracted with CH2Cl2
  4. dry with materialThe organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dc9abf91994846aa9f10be780ae403af
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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