Methanol → (RS)-(2,6-difluoro-4-isobutylcarbamoyl-phenyl)-ethoxy-acetic acid

HRID 1247376Notes

Reaction equation

HRID 1247376 reaction equation
C([O:3][C:4](=[O:24])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([C:16](=[O:22])[NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:11][C:10]=1[F:23])[O:6][CH2:7][CH3:8])C.CO.O.O[Li].O>C1COCC1.CCOC(C)=O>[F:15][C:14]1[CH:13]=[C:12]([C:16](=[O:22])[NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH:11]=[C:10]([F:23])[C:9]=1[CH:5]([O:6][CH2:7][CH3:8])[C:4]([OH:24])=[O:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 69291808(RS)-(2,6-difluoro-4-isobutylcarbamoyl-phenyl)-ethoxy-acetic acid ethyl ester

Product 1

HCID 21905565(RS)-(2,6-difluoro-4-isobutylcarbamoyl-phenyl)-ethoxy-acetic acidYield 66.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (RS)-(2,6-difluoro-4-isobutylcarbamoyl-phenyl)-ethoxy-acetic acid ethyl ester (125 mg) in a mixture of THF (1 ml), MeOH (1 ml) and H2O (0.5 ml) was added LiOH.H2O (31 mg). After stirring 1.5 h at 60° C. AcOEt was added (10 ml) and the product was extracted with H2O (10 ml). The aqueous layer was collected, acidified with 1 N HCl and extracted with AcOEt (2×15 ml). The combined organic layers were dried (Na2SO4) and the solvent is evaporated to obtain 76 mg (66%) of (RS)-(2,6-difluoro-4-isobutylcarbamoyl-phenyl)-ethoxy-acetic acid. Off-white solid. MS 333.4 ([M+H]+).

Workup

  1. extractionthe product was extracted with H2O (10 ml)
  2. customThe aqueous layer was collected
  3. extractionextracted with AcOEt (2×15 ml)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-0e820791d7ff4a49a9743feeb911e9f8
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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