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

HRID 2395193Notes

Reaction equation

HRID 2395193 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, under ice-cooling, 63.3 of triphenylphosphine, 29.5 g of benzoic acid and 42.0 g of diethyl azodicarboxylate, and the mixture was stirred in an argon atmosphere at room temperature for 6 hours. To the reaction mixture were added 800 ml of ethyl acetate and 500 ml of water to fractionate and the aqueous phase was extracted with 200 ml of ethyl acetate. The organic phases were collected, washed successively with water and with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated. The residue was purified by using silica gel chromatography (gradient eluent; hexane:ethyl acetate=15:1→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. temperaturecooling
  2. extractionthe aqueous phase was extracted with 200 ml of ethyl acetate
  3. customThe organic phases were collected
  4. washwashed successively with water and with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-93586ed0146840fea8465c701caabc3a
Source dataset
uspto-grants-1998_09
Patent number
US05814324

Reaction notes

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