Hydrochloric Acid → (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol

HRID 916675Notes

Reaction equation

HRID 916675 reaction equation
[Si]([O:8][C@H:9]([CH3:26])[C@:10]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25])([OH:17])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)(C(C)(C)C)(C)C.Cl.C1(C)C=CC=CC=1>CO>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[C@:10]([OH:17])([C@H:9]([OH:8])[CH3:26])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 58961305(2R, 3R)-3-(tert-butyldimethylsilyloxy)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Product 1

HCID 10286074(2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The (2R, 3R)-3-(tert-butyldimethylsilyloxy)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (12.2 g) synthesized in Example 12 was dissolved in methanol (41 mL). Hydrochloric acid (3 N, 21 g) was added to the solution and the mixture was stirred at 50° C. for four hours. Toluene (120 g) was added to the reaction mixture and was then stirred. Subsequently, an aqueous layer was separated. An aqueous solution (2 N, 41 g) of sodium hydroxide was added to the aqueous layer so that the pH of the mixture was controlled to be 9. The target compound was extracted with ethyl acetate (120 mL). The extracted organic layer was dried with anhydrous magnesium sulfate. The drying agent was filtered, and the filtrate was concentrated under reduced pressure. The resultant light yellow syrup was crystallized with toluene to recover-white crystals of the target compound (7.9 g, 92%). The values of the physical properties corresponded with those in Example 15. Diastereomeric excess: 99.5% de

Workup

  1. stirringwas then stirred
  2. customSubsequently, an aqueous layer was separated
  3. additionAn aqueous solution (2 N, 41 g) of sodium hydroxide was added to the aqueous layer so that the pH of the mixture
  4. extractionThe target compound was extracted with ethyl acetate (120 mL)
  5. dry with materialThe extracted organic layer was dried with anhydrous magnesium sulfate
  6. filtrationThe drying agent was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resultant light yellow syrup was crystallized with toluene to recover-white crystals of the target compound (7.9 g, 92%)

Sources & evidence

ORD record
ord-00088886e34f4c098d78060bfe55698a
Source dataset
uspto-grants-2007_09
Patent number
US07271185B2

Reaction notes

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