Benzoic Acid → [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]benzoate

HRID 482042Notes

Reaction equation

HRID 482042 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@H:12]([OH:14])[CH3:13])[CH2:11][O:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34](O)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@@H:12]([O:14][C:34](=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH3:13])[CH2:11][O:10]1

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10536015(1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol

Product 1

HCID 10709605[(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]benzoateYield 78.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 16.1 g of (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol in 320 ml of tetrahydrofuran were added, with ice cooling, 63.3 g of triphenylphosphine, 29.5 g of benzoic acid and 42.0 g of diethyl azodicarboxylate and the mixture was stirred at room temperature for six hours under an atmosphere of argon. To the reaction solution were added 800 ml of ethyl acetate and 500 ml of water to fractionate and the aqueous layer was extracted with 200 ml of ethyl acetate. The organic layers were combined, washed successively with water and a saturated aqueous solution of sodium chloride, then dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=15/1 to 7/1) to give 19.2 g of [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]benzoate as a colorless oil.

Workup

  1. extractionthe aqueous layer was extracted with 200 ml of ethyl acetate
  2. washwashed successively with water
  3. dry with materiala saturated aqueous solution of sodium chloride, then dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=15/1 to 7/1)

Sources & evidence

ORD record
ord-9601a5a717f544f68baa154bc18914f6
Source dataset
uspto-grants-1998_08
Patent number
US05792780

Reaction notes

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