Hydrochloric Acid → HCID 178442456, compound

HRID 216396Notes

Reaction equation

HRID 216396 reaction equation
Cl.[CH3:2][C:3]([CH3:47])([CH2:45][CH3:46])[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][C:41]([F:44])=[CH:40][N:39]=3)=[CH:34][CH:33]=2)[OH:31])[N:8](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1>CO>[CH3:2][C:3]([CH3:47])([CH2:45][CH3:46])[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][C:41]([F:44])=[CH:40][N:39]=3)=[CH:34][CH:33]=2)[OH:31])[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 686683162-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanol

Product 1

HCID 178442456HCID 178442456, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen chloride (4 M in dioxane) (1.5 mL, 0.67 mmol) was added to a solution of 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanol (200 mg, 0.33 mmol) in methanol (6 mL). After stirring at ambient temperature for 3 h, volatiles were removed. 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. Combined extracts were dried (magnesium sulfate) and concentrated in vacuo to afford the title compound. Purification by HPLC (Gilson; Chiralcel OJ column; 10 mL/min; 10% isopropanol/heptane). (M+H) found 368.

Workup

  1. customvolatiles were removed
  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 materialCombined extracts were dried (magnesium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab12c871fb2e4ff2bd71e51166012daf
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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