Sodium hydride → HCID 57167054, compound

HRID 654850Notes

Reaction equation

HRID 654850 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C@:10]([OH:26])([C@@H:17]([CH3:25])[C@@H:18](OS(C)(=O)=O)[CH3:19])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C@@:10]1([CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[C@@H:17]([CH3:25])[C@@H:18]([CH3:19])[O:26]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 57231627HCID 57231627, compound

Product 1

HCID 57167054HCID 57167054, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

11 mg of a 60% by weight dispersion of sodium hydride in mineral oil were added to a solution of 51 mg of (2R*,3S*,4S*)-2-(2-chlorophenyl)-4-(methanesulfonyloxy)-3-methyl-1-(1H-1,2,4-triazol-1-yl)-2-pentanol [which was synthesized by a similar procedure to that described in Preparation 2(b) and 2(c) and derived from the 4,5-epoxy compound having the lower polarity of the stereoisomers at the C4 position prepared by a similar procedure to that described in Preparation 2(a)] in 2 ml of dimethylformamide; the mixture was then stirred at 60° C. for 2 hours. At the end of this time, the mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting oily residue was purified by preparative thin layer chromatography on silica gel, using a 1:2 by volume mixture of hexane and ethyl acetate as the developing solvent, to afford 10 mg of the title compound as an oil.

Workup

  1. customwas synthesized by a similar procedure to
  2. customprepared by a similar procedure to
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resulting oily residue was purified by preparative thin layer chromatography on silica gel
  8. additionby volume mixture of hexane and ethyl acetate as the developing solvent

Sources & evidence

ORD record
ord-814a42f94bd84594ba768ba5c764c652
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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