1-(((2R,3S)-2-(2-fluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole → HCID 178462385, compound

HRID 1937146Notes

Reaction equation

HRID 1937146 reaction equation
C[O-].[Na+].[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C@@:11]1([CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[C@H:13]([CH3:14])[O:12]1.C([S:24][C@@H:25]1[CH2:30][O:29][C@@H:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:27][CH2:26]1)(=O)C>C(O)C>[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C@:11]([OH:12])([C@H:13]([S:24][C@@H:25]1[CH2:26][O:27][C@@H:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:29][CH2:30]1)[CH3:14])[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1

Participants

5

Reactant 3

HCID 104439761-(((2R,3S)-2-(2-fluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazoleHCID 10942334Sodium MethoxideHCID 178477153HCID 178477153, compound

Product 1

HCID 178462385HCID 178462385, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
87 °C

Procedure

0.12 ml (0.59 mmol) of a 4.9 M methanolic solution of sodium methoxide were added to a solution of 0.93 g (4.0 mmol) of (2R,3S)-2-(2-fluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane [prepared as described in Chem. Pharm. Bull., 43, 441-449 (1995)] and 1.14 g (4.8 mmol) of trans-5-(acetylthio)-2-phenyl-1,3-dioxane [prepared as described in Japanese Patent Application (Kokai) Hei 8-333350] in 15 ml of ethanol. The resulting mixture was stirred at 87° C. for 13 hours. After cooling, the reaction mixture was partitioned between ethyl acetate and an aqueous ammonium chloride solution. The organic solution was washed with saturated aqueous sodium chloride solution and then concentrated under reduced pressure. The resulting oily residue was purified by chromatography on a silica gel (75 g) column using a 3:2 mixture of ethyl acetate and hexane as the eluant to afford 0.68 g (yield 40%) of the title compound as a non-crystalline solid.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between ethyl acetate
  3. washThe organic solution was washed with saturated aqueous sodium chloride solution
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting oily residue was purified by chromatography on a silica gel (75 g) column
  6. additiona 3:2 mixture of ethyl acetate and hexane as the eluant

Sources & evidence

ORD record
ord-e01c39d81a3e4f3b8ca132972de8630b
Source dataset
uspto-grants-2002_05
Patent number
US06392082B1

Reaction notes

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