Hydrochloric Acid → HCID 57656244, compound

HRID 2041456Notes

Reaction equation

HRID 2041456 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]([F:30])[CH:18]=1)=O)(C)(C)C>ClCCl.C([O-])(O)=O.[Na+]>[CH3:26][C:25]([CH3:28])([CH3:27])[CH2:24][C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH2:15])=[CH:18][C:19]=1[F:30])=[O:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57656379HCID 57656379, compound

Product 1

HCID 57656244HCID 57656244, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Add 4N hydrogen chloride in dioxane (2.7 mL, 10.8 mmol) to a solution of N-(tert-butoxycarbonyl)-4-(3,3-dimethyl-butyryl)-3-fluoro-benzylamine (296 mg, 0.92 mmol) in dichloromethane (11 mL) and stir for 4 h. Concentrate in vacuo and wash the solid obtained with diethyl ether. Suspend the solid in 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 an oil (175 mg, 82%).

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-befb11f2fc094900ab750d8fac6af250
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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