Triethylamine → HCID 14706443, compound

HRID 1654214Notes

Reaction equation

HRID 1654214 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:19])([C@@H:16]([OH:18])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:19])([C@@H:16]([O:18][S:28]([CH3:27])(=[O:30])=[O:29])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14706434HCID 14706434, compound

Product 1

HCID 14706443HCID 14706443, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In ethyl acetate (4 ml) was dissolved (2R,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (0.18 g). To the solution were added triethylamine (0.10 ml) and methanesulfonyl chloride (84 mg) under ice-cooling. The mixture was stirred for 30 minutes at room temperature, to which was added ethyl acetate (10 ml). The reaction mixture was washed with water and dried (anhydrous magnesium sulfate), followed by concentration to give (2R,3S)-2-(2,4-difluorophenyl)-3-methanesulfonyloxy-1-(1H-1,2,4-triazol-1-yl)-2-butanol as an oily product. This product was dissolved in methanol (6 ml), to which was added a 5.6% methanol solution of sodium methylate (0.76 ml) under ice-cooling. The mixture was stirred for 30 minutes at room temperature, which was then concentrated under reduced pressure. To the concentrate was added ethyl acetate (30 ml), which was washed with water and dried (anhydrous magnesium sulfate). The solvent was then distilled off, and the residue was purified by means of a silica gel chromatography (eluent: hexane-ethyl acetate=1:2) to afford (2R,3R)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane (0.15 g) as a colorless oily product.

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with water
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-9c6001bf526144abaafe208dbc0ccc63
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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