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

HRID 602047Notes

Reaction equation

HRID 602047 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:23]([CH2:30][CH3:31])[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]([CH:23]([CH2:30][CH3:31])[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 86638766ethyl 3-[3,4-difluoro-5-((1S)-1-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenyl]pentanoate

Product 1

HCID 57470583Ethyl 3-{3,4-difluoro-5-[(2S)-2-oxiranyl]phenyl}pentanoateYield 96%

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]pentanoate (14.50 g, 0.0318 mol) in absolute ethanol (270 mL) was added potassium carbonate (8.78 g, 0.0635 mol) and the reaction was stirred at RT overnight. The reaction was concentrated and diluted with water and extracted with ethyl acetate (×2). The combined organic layers were dried over Na2SO4, filtered, and concentrated. Column chromatography (hexane:ethylacetate, 0-25%) yielded the desired product (8.65 g, 96%).

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate (×2)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8ef8cc3c58b24eeda69e61c2093f7f8a
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

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