Hydrochloric Acid → HCID 178461659, compound

HRID 850085Notes

Reaction equation

HRID 850085 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:33])([C@H:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28](COCC)[N:27]=[N:26][CH:25]=2)=[CH:20][CH:19]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.Cl>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:33])([C@H:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]=[N:27][NH:26][CH:25]=2)=[CH:20][CH:19]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70040338HCID 70040338, compound

Product 1

HCID 178461659HCID 178461659, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2R,3S)-2-(2,4-difluorophenyl)-3-(4-[1-ethoxymethyl-1,2,3-triazol-5-yl]phenyl)-1-(1,2,4-triazol-1-yl)butan-2-ol (5.2 g, 0.11 mol-see Example 25) in ethanol (50 ml) was treated with dilute hydrochloric acid (2N, 12 ml) and the mixture was heated under reflux for one hour. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was dissolved in water (50 ml) and the mixture was neutralized by addition of solid sodium carbonate and was extracted with ethyl acetate (2×100 ml). The combined extracts were dried (MgSO4) and evaporated under reduced pressure to yield a colourless foam. The crude product was purified by column chromatography on silica by elution with ethyl acetate/diethylamine (95:5) followed by ethyl acetate/methanol (90:10 then 80:20). Fractions containing the desired product were combined and evaporated under reduced pressure to yield the title compound as a colourless foam (3.7 g, 82%), [α]D25 =-63.8°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hour
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in water (50 ml)
  5. additionthe mixture was neutralized by addition of solid sodium carbonate
  6. extractionwas extracted with ethyl acetate (2×100 ml)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customevaporated under reduced pressure
  9. customto yield a colourless foam
  10. customThe crude product was purified by column chromatography on silica by elution with ethyl acetate/diethylamine (95:5)
  11. additionFractions containing the desired product
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8959836a3d7246408416b094be6962dd
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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