Hydrochloric Acid → HCID 178442449, compound

HRID 216372Notes

Reaction equation

HRID 216372 reaction equation
Cl.[CH3:2][C:3]([CH3:46])([CH2:44][CH3:45])[CH2:4][C:5]1[N:6]=[C:7]([CH2:29][CH:30]([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:34][CH:33]=2)[F:31])[N:8](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1>CO>[CH3:2][C:3]([CH3:46])([CH2:44][CH3:45])[CH2:4][C:5]1[N:6]=[C:7]([CH2:29][CH:30]([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:34][CH:33]=2)[F:31])[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68667503HCID 68667503, compound

Product 1

HCID 178442449HCID 178442449, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen chloride (4 M in 1,4-dioxane) (4 mL, 1 mmol) was added to an ambient temperature solution of 2-(4-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-fluoroethyl}phenyl)pyridine (240 mg, 0.4 mmol) in methanol (20 mL). After stirring at ambient temperature for 3 h, volatiles were removed in vacuo. The residue was partitioned between 1 N hydrochloric acid and diethyl ether. The aqueous phase was washed with diethyl ether, basified with saturated aqueous sodium carbonate and extracted with diethyl ether and ethyl acetate. The combined extracts were dried (magnesium sulfate) and concentrated in vacuo to afford the title compound. High pressure liquid chromatography (Chiralcel OJ column) eluting with 15% ethanol/hexane afforded the separate enantiomers. (M+H) found 352.

Workup

  1. customvolatiles were removed in vacuo
  2. customThe residue was partitioned between 1 N hydrochloric acid and diethyl ether
  3. washThe aqueous phase was washed with diethyl ether
  4. extractionextracted with diethyl ether and ethyl acetate
  5. dry with materialThe combined extracts were dried (magnesium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4bb9385bdefe4452af032fd688f97957
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

Loading…