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

HRID 279159Notes

Reaction equation

HRID 279159 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>[C:34]([O:14][C@H:12]([C@@:9]1([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH2:11][O:10]1)[CH3:13])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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 an ice-cooled solution of (1R)-1-[(2R)-2-(2,4-di-fluorophenyl)-2-oxiranyl]ethanol (16.1 g) in tetrahydrofuran (320 ml) were added triphenylphosphine (63.3 g), benzoic acid (29.5 g) and diethyl azodicarboxylate (42.0 g). The mixture was stirred at room temperature for 6 hours under an argon atmosphere. After ethyl acetate (800 ml) and water (500 ml) were added thereto, the separated aqueous layer was extracted with ethyl acetate (200 ml). The combined organic layers were washed with water and a saturated aqueous solution of sodium chloride successively, 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 [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] benzoate (19.2 g) as a colorless oily substance.

Workup

  1. extractionthe separated aqueous layer was extracted with ethyl acetate (200 ml)
  2. washThe combined organic layers were washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride successively, 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-48f168618e5e4b11ab44af2f5b3dbed3
Source dataset
uspto-grants-2002_03
Patent number
US06362206B1

Reaction notes

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