Hydrochloric Acid → HCID 18955393, compound

HRID 1451951Notes

Reaction equation

HRID 1451951 reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7](=[O:27])[C:8]([F:26])([F:25])[C:9]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24])([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)([CH3:5])[CH3:4].[H-].[Na+].[CH3:30]I.Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH3:30][O:1][CH2:2][C:3]([NH:6][C:7](=[O:27])[C:8]([F:25])([F:26])[C:9]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24])([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)([CH3:5])[CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19973113HCID 19973113, compound

Product 1

HCID 18955393HCID 18955393, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 2 ml of N,N-dimethylformamide was dissolved 0.1 g of N-(1-hydroxy-2-methylpropan-2-yl)-3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanamide. To the resulting solution was added 0.012 g of 60% sodium hydride at 0°-5° C. The solution was subjected to reaction at 20°-25° C. for 30 minutes. To the reaction mixture was added 0.04 g of methyl iodide at 0°-5° C. The resulting mixture was subjected to reaction at 20°-25° C. for 12 hours. The reaction mixture was introduced into a mixed solvent consisting of 10 ml of ethyl acetate and 5 ml of water. The resulting solution was adjusted to pH 2.0 with 6N hydrochloric acid. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluant: chloroform/methanol=100/1) to obtain 30 mg of N-(1-methoxy-2-methylpropan-2-yl)-3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4- (1H-1,2,4-triazol-1-yl)butanamide.

Workup

  1. customThe solution was subjected to reaction at 20°-25° C. for 30 minutes
  2. customThe resulting mixture was subjected to reaction at 20°-25° C. for 12 hours
  3. additionThe reaction mixture was introduced into a mixed solvent
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThereafter, the solvent was removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by a column chromatography (eluant: chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-2c270125f4954a0b86ee41a66e03dec6
Source dataset
uspto-grants-1997_02
Patent number
US05605921

Reaction notes

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