Triethylamine → (2S,3S)-2-(2,4-difluorophenyl)-3-methanesulfonyloxy-1-(1H-1,2,4-triazol-1-yl)-2-butanol

HRID 1654193Notes

Reaction equation

HRID 1654193 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.ClCCl>[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

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11054699(2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol

Product 1

HCID 22852537(2S,3S)-2-(2,4-difluorophenyl)-3-methanesulfonyloxy-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

In a mixture of ethyl acetate (2 ml) and dichloromethane (0.5 ml) was dissolved (2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (58 mg). To the solution were added, under ice-cooling, triethylamine (66 μl) and methanesulfonyl chloride (37 μl). The mixture was stirred for two hours at room temperature. To the reaction mixture was added ethyl acetate (30 ml), which was washed with water, dried (anhydrous magnesium sulfate) and concentrated to afford (2S,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 (2 ml), to which was added, under ice-cooling, 28% sodium methyl ate (116 μl), and the mixture was stirred for 30 minutes at room temperature. To the reaction mixture was added dichloromethane (30 ml), which was washed with water and dried (anhydrous magnesium sulfate), followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel chromatography (eluent: ethyl acetate-dichloromethane=4:1 ), followed by crystallization from hexane to afford (2S,3R)-2-(2,4-difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyl oxirane (42 mg) as colorless needles. m.p. 89°-90° C. [α]D23 =+7.8° (c=1.0 in MeOH)

Workup

  1. additionTo the solution were added, under ice-
  2. temperaturecooling
  3. washwas washed with water
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2e8151d14b584c499c66cc0d95ea3531
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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