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

HRID 1250374Notes

Reaction equation

HRID 1250374 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-b4afd25cfa144daca6d909f13699d986
Source dataset
uspto-grants-2002_01
Patent number
US06337403B1

Reaction notes

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