Hydrochloric Acid → HCID 69057401, compound

HRID 1435080Notes

Reaction equation

HRID 1435080 reaction equation
C(OC(=O)[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[NH2:27])=[CH:22][C:21]=2[CH3:29])=[C:16]([CH3:30])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.[ClH:32]>C(OCC)(=O)C.O1CCOCC1.C(O)(C)C>[ClH:32].[CH3:29][C:21]1[CH:22]=[C:23]([C:26]([NH2:27])=[O:28])[CH:24]=[CH:25][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([CH2:13][NH:7][CH2:8][CH2:9][CH:10]([CH3:11])[CH3:12])=[CH:15][C:16]=1[CH3:30]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57937817HCID 57937817, compound

Product 1

HCID 69057401HCID 69057401, compound

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

(4′-Carbamoyl-2′,2-dimethyl-biphenyl-4-ylmethyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester (I-2e: 12 g, 28.3 mmol) was dissolved in ethyl acetate and treated with 20 mL of 4.0 M hydrogen chloride in dioxane. After stirring overnight at room temperature, the volatiles were removed under reduced pressure and the resulting crude material dissolved in methanol and then ethyl acetate was added to precipitate a white solid that was isolated via filtration. This solid was suspended in iso-propanol (1 g: 20 mL), heated at reflux for 20 minutes and stirred overnight at room temperature. The resulting slurry was collect via filtration, rinsing with chilled iso-propanol, and dried under vacuum to provide the title compound (E2-01).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. dissolutionthe resulting crude material dissolved in methanol
  3. additionethyl acetate was added
  4. customto precipitate a white solid
  5. customthat was isolated via filtration
  6. temperatureheated
  7. temperatureat reflux for 20 minutes
  8. stirringstirred overnight at room temperature
  9. filtrationThe resulting slurry was collect via filtration
  10. washrinsing with chilled iso-propanol
  11. customdried under vacuum

Sources & evidence

ORD record
ord-cbfdf7020ee8477a9380b3604044feb8
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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