Methyl 2,2,2-trichloroacetimidate → Methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-(trichloromethyl)-1H-benzimidazole-6-carboxylate

HRID 1521686

Reaktionsgleichung

Reaktionsgleichung von HRID 1521686
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[Cl:24][C:25]([Cl:31])([Cl:30])[C:26](=N)OC>C(O)(=O)C>[C:20]([O:19][C:17]([NH:16][CH2:15][CH2:14][CH2:13][N:12]1[C:3]2[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=2[N:1]=[C:26]1[C:25]([Cl:31])([Cl:30])[Cl:24])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Komponenten

4

Edukt 2

HCID 100479Methyl 2,2,2-trichloroacetimidateHCID 11962077Methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoate

Produkt 1

HCID 67236445Methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-(trichloromethyl)-1H-benzimidazole-6-carboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoate (4.7 g, 14.5 mmol) in acetic acid (50 mL) is added methyl trichloroacetimidate (3.1 g, 17.4 mmol). After 3 h at room temperature, the solvent is evaporated, the residue is dissolved in EtOAc, and is washed with Na2CO3 and brine. The organic layer is dried (Na2SO4) and evaporated. The residue is triturated with hexanes to afford the title compound (5.2 g, 80%) as a fine powder. LCMS (Method T), 1.85 min, 450.63 (MH+).

Aufarbeitung

  1. customthe solvent is evaporated
  2. dissolutionthe residue is dissolved in EtOAc
  3. washis washed with Na2CO3 and brine
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. customevaporated
  6. customThe residue is triturated with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9060c1155b03415da17abcf4f32591ef
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073926B2

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