Hydrogen Bromide → HCID 19973070, compound

HRID 2380323Notes

Reaction equation

HRID 2380323 reaction equation
Br.ClC1C=CC(CN[C:9](=[O:29])[C:10]([F:28])([F:27])[C:11]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])([OH:18])[CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)=CC=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-:40].[Na+].[Na+]>O>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[C:11]([OH:18])([CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)[C:10]([F:27])([F:28])[C:9]([OH:29])=[O:40]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 1140TolueneHCID 10340Sodium CarbonateHCID 15234052HCID 15234052, compound

Product 1

HCID 19973070HCID 19973070, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4 ml of 47% hydrobromic acid was added 500 mg of N-(4-chlorobenzyl)-3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanamide. The resulting mixture was refluxed for 6 hours. Thereto were added 20 ml of toluene and 20 ml of water. The resulting solution was adjusted to pH 8.5 with sodium carbonate. The aqueous layer was separated and 20 ml of ethyl acetate was added thereto. The resulting mixture was adjusted to pH 1.0 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 to obtain 230 mg of 3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butyric acid.

Workup

  1. temperatureThe resulting mixture was refluxed for 6 hours
  2. customThe aqueous layer was separated
  3. addition20 ml of ethyl acetate was added
  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

Sources & evidence

ORD record
ord-64f6445baf7b4bbb882a5dfd41682e3a
Source dataset
uspto-grants-1994_11
Patent number
US05366989

Reaction notes

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