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

HRID 1654213Notes

Reaction equation

HRID 1654213 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 9816851(2S,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol

Product 1

HCID 57187735(2S,3R)-2-(2,4-difluorophenyl)-3-methanesulfonyloxy-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In ethyl acetate (40 ml) was dissolved (2S,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (2.5 g). To the solution were added, under ice-cooling, triethylamine (1.82 ml) and methanesulfonyl chloride (1.51 g). The mixture was stirred for 30 minutes at room temperature. To the reaction mixture was added ethyl acetate (40 ml), which was washed with water and dried (anhydrous magnesium sulfate), followed by concentration to give (2S,3R)-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 (40 ml), to which was added, under ice-cooling, a 28% methanol solution of sodium methylate (2.04 g). The mixture was stirred for 30 minutes at room temperature, then the reaction mixture was concentrated under reduced pressure. To the concentrate was added ethyl acetate (100 ml), which was washed with water, followed by drying (anhydrous magnesium sulfate). The solvent was distilled off under reduced pressure, and the residue was purified by means of a silica gel chromatography (eluent: ethyl acetate-dichloromethane=4:1) to give (2S,3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane (1.62 g) as a colorless oily product. This product became a colorless solid in a freezer. m.p. 41°-43° C. [α]D23 =+5.8° (c=1.0 in methanol)

Workup

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

Sources & evidence

ORD record
ord-bd822f39c28647b3ab17529db5e7274e
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

Loading…