Potassium Carbonate → HCID 10807230, compound

HRID 2395688Notes

Reaction equation

HRID 2395688 reaction equation
Br[CH2:2][C:3]([NH2:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C@:20]([OH:30])([C@H:27]([SH:29])[CH3:28])[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1>CN(C)C=O.C1C=CC=CC=1>[C:3]([CH2:2][S:29][C@H:27]([CH3:28])[C@:20]([C:14]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=1[F:12])([OH:30])[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)(=[O:4])[NH2:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 1922642-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Product 1

HCID 10807230HCID 10807230, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

58 mg (0.42 mmole) of 2-bromoacetamide and 48 mg (0.35 mmole) of potassium carbonate were added to a solution of 100 mg (0.35 mmole) of (2R,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol in 3 ml of anhydrous dimethylformamide, and the mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was diluted with benzene and washed with a saturated aqueous solution of sodium chloride, after which the solvent was removed by distillation under reduced pressure. The virtually pure product thus obtained was recrystallized from a mixture of acetone and hexane to afford 90 mg of the title compound, melting at 144°-145° C.

Workup

  1. washwashed with a saturated aqueous solution of sodium chloride
  2. customafter which the solvent was removed by distillation under reduced pressure
  3. customThe virtually pure product thus obtained
  4. customwas recrystallized from a mixture of acetone and hexane

Sources & evidence

ORD record
ord-136f53380931491799a5dd3c6739ec12
Source dataset
uspto-grants-1996_02
Patent number
US05489606

Reaction notes

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