Hydrochloric Acid → HCID 57656133, compound

HRID 2041530Notes

Reaction equation

HRID 2041530 reaction equation
Cl.C(OC([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:23])[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:13][CH:12]=1)=O)(C)(C)C>O1CCOCC1.CCOC(C)=O>[CH3:23][CH:17]([C:14]1[CH:13]=[CH:12][C:11]([CH2:10][NH2:9])=[CH:16][CH:15]=1)[CH2:18][C:19]([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57656318HCID 57656318, compound

Product 1

HCID 57656133HCID 57656133, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4N hydrogen chloride in dioxane (10 mL) to a stirred solution of N-(tert-butoxycarbonyl)-4-(1,3,3-trimethyl-butyl)-benzylamine (225 mg, 0.74 mmol) in EtOAc (15 mL) and stir the mixture at ambient temperature overnight. Concentrate in vacuo and wash the solid with diethyl ether. Suspend the solid in dichloromethane and saturated aqueous NaHCO3 and stir until both phases are clear (15 min). Extract the aqueous phase twice with dichloromethane. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to give the title compound as an oil (0.136 g, 90%) that was used without any further purification. MS (ES+) m/z: 206 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. washwash the solid with diethyl ether
  3. stirringsaturated aqueous NaHCO3 and stir until both phases
  4. custom(15 min)
  5. extractionExtract the aqueous phase twice with dichloromethane
  6. dry with materialDry the combined organic extracts over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f854ca0738c746d6af8cd4867bb6fed3
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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