Triethylamine → HCID 54209931, compound

HRID 2397017Notes

Reaction equation

HRID 2397017 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C@:16]([OH:32])([C@H:23]([N:25]1[CH:29]=[C:28]([CH2:30][OH:31])[N:27]=[N:26]1)[CH3:24])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl>[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C@:16]([OH:32])([C@H:23]([N:25]1[CH:29]=[C:28]([CH2:30][O:31][S:34]([CH3:33])(=[O:36])=[O:35])[N:27]=[N:26]1)[CH3:24])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53770267HCID 53770267, compound2×

Product 1

HCID 54209931HCID 54209931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.26 ml) was added dropwise to a solution of (2R,3R)-2-(2,4-difluorophenyl)-3-(4-hydroxy methyl-1H-1,2,3-triazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (Compound 56, 0.6 g) and methanesulfonyl chloride (0.14 ml) in dichloromethane (20 ml) under ice-cooling. The mixture was stirred for 30 minutes at room temperature. After addition of dichloromethane (20 ml), the mixture was washed with water (20 ml) and 5% sodium hydrogen carbonate aqueons solution (20 ml). The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to give (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methanesulfonyloxymethyl-1H-1,2,3-triazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol as colorless oil.

Workup

  1. temperaturecooling
  2. washthe mixture was washed with water (20 ml) and 5% sodium hydrogen carbonate aqueons solution (20 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-d3063240280b4bb693be642f1b1a841b
Source dataset
uspto-grants-1996_02
Patent number
US05495024

Reaction notes

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