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

HRID 1250372Notes

Reaction equation

HRID 1250372 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-115f11ba07c9497a9d28fe03b8d53543
Source dataset
uspto-grants-2002_01
Patent number
US06337403B1

Reaction notes

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