Hydrochloric Acid → HCID 178442231, compound

HRID 216369Notes

Reaction equation

HRID 216369 reaction equation
Cl.[CH3:2][C:3]([CH3:45])([CH3:44])[CH2:4][C:5]1[N:6]=[C:7]([CH2:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[S:43][N:42]=[CH:41][CH:40]=3)=[CH:35][CH:34]=2)([OH:32])[CH3:31])[N:8](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1>CO>[CH3:2][C:3]([CH3:45])([CH3:44])[CH2:4][C:5]1[N:6]=[C:7]([CH2:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[S:43][N:42]=[CH:41][CH:40]=3)=[CH:35][CH:34]=2)([OH:32])[CH3:31])[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 686677351-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-2-(4-isothiazol-5-ylphenyl)propan-2-ol

Product 1

HCID 178442231HCID 178442231, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Hydrogen chloride (4 M in 1,4-dioxane) (2 mL, 0.5 mmol) was added to an ambient temperature solution of 1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-2-(4-isothiazol-5-ylphenyl)propan-2-ol (103 mg, 0.17 mmol) in methanol (4 mL). After stirring at 70° C. for 1 h, volatiles were removed in vacuo. The residue was basified with 10% aqueous sodium hydroxide and extracted with ethyl acetate. Combined extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride afforded the title compound. LCMS: 356 (M+H). Individual enantiomer (E1 or E2) was obtained by HPLC separation on a chrial column.

Workup

  1. customvolatiles were removed in vacuo
  2. extractionextracted with ethyl acetate
  3. dry with materialCombined extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ab0ea22298141a9af97812c2a00bfaf
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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