(2R,3S)-2-(4-Fluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane → HCID 178462387, compound

HRID 1936844Notes

Reaction equation

HRID 1936844 reaction equation
C[O-].[Na+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@@:11]2([CH2:15][N:16]3[CH:20]=[N:19][CH:18]=[N:17]3)[C@H:13]([CH3:14])[O:12]2)=[CH:7][CH:6]=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][C:8]([C@:11]([OH:12])([C@H:13]([S:24][C@H:25]2[CH2:26][O:27][C@@H:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:29][CH2:30]2)[CH3:14])[CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 10443975(2R,3S)-2-(4-Fluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxiraneHCID 10942334Sodium MethoxideHCID 178477152HCID 178477152, compound

Product 1

HCID 178462387HCID 178462387, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1 ml (0.59 mmol) of a 4.8 M methanolic solution of sodium methoxide was added to a solution of 2.33 g (10 mmol) of (2R,3S)-2-(4-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 2.38 g (10 mmol) of cis-5-(acetylthio)-2-phenyl-1,3-dioxane [prepared as descripted in Step 6(i) above] in 40 ml of ethanol. The resulting mixture was stirred at 80° C. for 5 hours. After cooling, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel (50 g) column using a 2:1 mixture of ethyl acetate and hexane as the eluant to afford 3.1 g (yield 72%) of the title compound as a brown foamy solid.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel (50 g) column
  8. additiona 2:1 mixture of ethyl acetate and hexane as the eluant

Sources & evidence

ORD record
ord-9988da6150244dbaa1e3e57f425bf59a
Source dataset
uspto-grants-2002_05
Patent number
US06391903B1

Reaction notes

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