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

HRID 1937150Notes

Reaction equation

HRID 1937150 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C@:9]([OH:31])([C@H:16]([S:18][C@H:19]2[CH2:24][O:23][C@@H](C3C=CC=CC=3)[O:21][CH2:20]2)[CH3:17])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+]>CO>[F:2][C:3]1[CH:8]=[CH:7][C:6]([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]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178462387HCID 178462387, compound

Product 1

HCID 69944000(2R,3R)-2-(4-fluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanolYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 ml (12 mmol) of 12 N hydrochloric acid were added to a solution of 3.1 g (7.2 mmol) of (2R,3R)-2-(4-fluorophenyl)-3-[(cis-2-phenyl-1,3-dioxan-5-yl)thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol [prepared as described in Step 6(ii) above] in 39 ml of methanol. The resulting mixture was stirred at ambient temperature for 16 hours. At the end of this time, an aqueous sodium hydrogen carbonate solution was carefully added to the reaction mixture until the solution became weakly alkaline. Most of the methanol was evaporated from the mixture under reduced pressure. The resulting residue was then partitioned between ethyl acetate and aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel (30 g) column using a 1:9 mixture of methanol and ethyl acetate as the eluant to afford 2.15 g (yield 87%) of the title compound as a hygroscopic pale brown foamy solid.

Workup

  1. customMost of the methanol was evaporated from the mixture under reduced pressure
  2. customThe resulting residue was then partitioned between ethyl acetate and aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography on a silica gel (30 g) column
  6. additiona 1:9 mixture of methanol and ethyl acetate as the eluant

Sources & evidence

ORD record
ord-74e1464fb5a5421fbb9241006a181d1c
Source dataset
uspto-grants-2002_05
Patent number
US06392082B1

Reaction notes

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