Hydrochloric Acid → (R)-4-[(1-Methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamine

HRID 1191046Notes

Reaction equation

HRID 1191046 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](=[O:25])[NH:18][C@H:19]([CH3:24])[C:20]([F:23])([F:22])[F:21])=[CH:12][CH:11]=1)=O)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[CH3:24][C@@H:19]([NH:18][C:17]([CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH2:8])=[CH:15][CH:14]=1)=[O:25])[C:20]([F:23])([F:21])[F:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58495584(R)-N-(tert-Butoxycarbonyl)-4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamine

Product 1

HCID 58495445(R)-4-[(1-Methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamineYield 93.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Dissolve (R)—N-(tert-butoxycarbonyl)-4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamine (155 mg, 0.43 mmol) in DCM (8 mL). Add 4M hydrogen chloride in dioxane (0.85 mL) and stir at room temperature overnight. Concentrate in vacuo and partition the hydrochloride salt between saturated aqueous NaHCO3 and EtOAc. Extract the aqueous phase twice with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to obtain the title compound (105 mg, 91%). MS (ES+) m/z: 261 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. custompartition the hydrochloride salt between saturated aqueous NaHCO3 and EtOAc
  3. extractionExtract the aqueous phase twice with EtOAc
  4. dry with materialDry the combined organic extracts over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-ea4fa424844044a48e52b1f8e96be3d3
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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