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

HRID 1191046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191046
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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 58495445(R)-4-[(1-Methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamineAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ea4fa424844044a48e52b1f8e96be3d3
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680091B2

Notizen zur Reaktion

Wird geladen…