Hydrochloric Acid → (2R,3R)-2-(2-Fluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol

HRID 1937147Notes

Reaction equation

HRID 1937147 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C@:9]([OH:31])([C@H:16]([S:18][C@@H:19]1[CH2:24][O:23][C@@H](C2C=CC=CC=2)[O:21][CH2:20]1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1>C1(C)C=CC=CC=1>[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C@:9]([OH:31])([C@H:16]([S:18][CH:19]([CH2:20][OH:21])[CH2:24][OH:23])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178462385HCID 178462385, compound

Product 1

HCID 69944239(2R,3R)-2-(2-Fluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanolYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

110 ml (110 mmol) of 1 N hydrochloric acid were added to a solution of 13 g (30.3 mmol) of (2R,3 R)-2-(2-fluorophenyl)-3-[(trans-2-phenyl-1,3-dioxan-5-yl)thio]-1-(1H-1,2,4-triazol-1-yl)-2 -butanol [prepared as described in Step 5(i) above] in 80 ml of toluene. The resulting mixture was heated at 50° C. for 2.5 hours. At the end of this time, the water layer was separated and the oily layer was extracted twice with dilute hydrochloric acid and then with an aqueous sodium chloride solution. The aqueous layers were combined and sodium hydrogen carbonate was carefully added thereto in small portions until bubbles of carbon dioxide were no longer detected. The resulting mixture was extracted with ethyl acetate and the extract was then concentrated under reduced pressure to afford a solid residue. This residue was collected by filtration and then washed with a small amount of ethyl acetate to afford 5.57 g (yield 55%) of the title compound as a pale brown solid.

Workup

  1. customAt the end of this time, the water layer was separated
  2. extractionthe oily layer was extracted twice with dilute hydrochloric acid
  3. additionsodium hydrogen carbonate was carefully added
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. concentrationthe extract was then concentrated under reduced pressure
  6. customto afford a solid residue
  7. filtrationThis residue was collected by filtration
  8. washwashed with a small amount of ethyl acetate

Sources & evidence

ORD record
ord-022dc86307234410bbfc9e35cba36348
Source dataset
uspto-grants-2002_05
Patent number
US06392082B1

Reaction notes

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