Potassium Carbonate → Ethyl 3-{3,4-difluoro-5-[(2S)-2-oxiranyl]phenyl}propanoate

HRID 602037Notes

Reaction equation

HRID 602037 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:5]=[C:6]([C@H:9]([OH:22])[CH2:10]OS(C2C=CC(C)=CC=2)(=O)=O)[C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:5]=[C:6]([C@H:9]2[CH2:10][O:22]2)[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86638765Ethyl 3-[3,4-difluoro-5-((1S)-1-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenyl]propanoate

Product 1

HCID 57470574Ethyl 3-{3,4-difluoro-5-[(2S)-2-oxiranyl]phenyl}propanoateYield 82.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-[3,4-difluoro-5-((1S)-1-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenyl]propanoate (22.5 g, 52.5 mmol) in absolute ethanol (430 mL) was added potassium carbonate (7.27 g, 52.6 mmol) and the reaction was stirred at RT for 4 days. The reaction was concentrated and diluted with water and extracted with ethyl acetate (×2). The combined organic layers were washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. Purification by column chromatography (0-25% ethyl acetate:hexane) afforded the desired product (11.07 g, 82%).

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate (×2)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography (0-25% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-d76539625daa4dc7ae5fd3ae6c0f70e8
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

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