m-Chloroperbenzoic acid → HCID 57140205, compound

HRID 654866Notes

Reaction equation

HRID 654866 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C@:20]([OH:31])([C@@H:27]([CH3:30])[CH:28]=[CH2:29])[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1>C(Cl)Cl.C(OCC)(=O)C>[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C@:20]([OH:31])([C@@H:27]([CH3:30])[C@@H:28]1[O:6][CH2:29]1)[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57306297HCID 57306297, compound

Product 1

HCID 57140205HCID 57140205, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.360 g (6.19 mmole) of 3-chloroperoxybenzoic acid of 80% purity) were added at 0° C. to a solution of 960 mg (3.44 mmole) of (2R*,3S*)-2-(2,4-difluorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)-4-penten-2-ol (which was synthesized following the procedure disclosed in Japanese Patent Provisional Publication No. Sho 60-36468) in 30 ml of methylene chloride. Five minutes after the addition, the reaction mixture was stirred, and this stirring was continued overnight at room temperature. The reaction mixture was then diluted with ethyl acetate, after which it was washed, in turn, with an aqueous solution of sodium sulfite, with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride. After it had been dried, the mixture was freed from the solvent by distillation under reduced pressure. The resulting residue was subjected to column chromatography through silica gel, using a 1:2 by volume mixture of ethyl actate and hexane as the eluent, to afford 320 mg of stereoisomer A of the title compound (having the lower polarity), melting at 160°-180° C. and 206 mg of the desired stereoisomer B of the title compound (having the higher polarity) as an oil.

Workup

  1. customwas synthesized
  2. additionFive minutes after the addition
  3. washafter which it was washed, in turn, with an aqueous solution of sodium sulfite, with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride
  4. customAfter it had been dried
  5. distillationthe mixture was freed from the solvent by distillation under reduced pressure
  6. additionby volume mixture of ethyl actate and hexane as the eluent

Sources & evidence

ORD record
ord-0a89eb6add1f42c18b367fbe121f5c6d
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

Loading…