Hydrochloric Acid → HCID 57656563, compound

HRID 911594Notes

Reaction equation

HRID 911594 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])=[CH:19][C:18]=1[F:30])=O)(C)(C)C.C([O-])(O)=O.[Na+]>ClCCl>[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])=[C:18]([F:30])[CH:19]=1)=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 57656601HCID 57656601, compound

Product 1

HCID 57656563HCID 57656563, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 4N hydrogen chloride in dioxane (5.5 mL, 22 mmol) to a solution of N-(tert-butoxycarbonyl)-4-(3,3-dimethyl-butyryl)-2-fluoro-benzylamine (600 mg, 1.85 mmol) in dichloromethane (22 mL) and stir for 6.5 h. Concentrate in vacuo and wash the solid obtained with diethyl ether. Suspend the solid into saturated aqueous NaHCO3 and stir for 30 min. Extract the aqueous phase twice with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to obtain the title compound as an oil (420 mg, 99%).

Workup

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

Sources & evidence

ORD record
ord-1d008622a3b1413d9eea17401871c20d
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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