Hydrochloric Acid → HCID 57655942, compound

HRID 2041463Notes

Reaction equation

HRID 2041463 reaction equation
Cl.O1CCOCC1.C(OC([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:29])[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:19]([Cl:30])[CH:18]=1)=O)(C)(C)C.C([O-])(O)=O.[Na+]>ClCCl>[Cl:30][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[C:23](=[O:29])[CH2:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:16][NH2:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 57655904HCID 57655904, compound

Product 1

HCID 57655942HCID 57655942, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 4N hydrogen chloride in dioxane (0.9 mL, 3.6 mmol) to a solution of N-(tert-butoxycarbonyl)-3-chloro-4-(3,3-dimethyl-butyryl)-benzylamine (100 mg, 0.3 mmol) in dichloromethane (6 mL) and stir overnight. Concentrate in vacuo and wash the solid obtained with diethyl ether. Suspend the solid into saturated aqueous NaHCO3 and stir for 30 min. Extract twice with dichloromethane. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to obtain the title compound as a yellow oil (66 mg, 92%).

Workup

  1. concentrationConcentrate in vacuo
  2. washwash the solid
  3. customobtained with diethyl ether
  4. stirringstir for 30 min
  5. extractionExtract twice with dichloromethane
  6. dry with materialDry the combined organic extracts over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-8c677adf724a4a898031b9dd86afa241
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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