Hydrogen chloride-ethyl acetate → N-[(1S)-2-({6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}oxy)-1-methylethyl]acetamide

HRID 1026205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026205
[CH:1]1([CH2:4][O:5][C:6]2[CH:32]=[CH:31][C:9]3[N:10]=[C:11]([C:13]4[N:18]=[CH:17][C:16]([O:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:30])OC(C)(C)C)[CH3:22])=[CH:15][CH:14]=4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.Cl.[C:34](OCC)(=O)C>C(OCC)(=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:32]=[CH:31][C:9]3[N:10]=[C:11]([C:13]4[N:18]=[CH:17][C:16]([O:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:30])[CH3:34])[CH3:22])=[CH:15][CH:14]=4)[O:12][C:8]=3[CH:7]=2)[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86666262tert-butyl [(1S)-2-({6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}oxy)-1-methylethyl]carbamate

Produkt 1

HCID 57344093N-[(1S)-2-({6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}oxy)-1-methylethyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl [(1S)-2-({6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}oxy)-1-methylethyl]carbamate (350 mg) in ethyl acetate (20 mL) was added 4M hydrogen chloride/ethyl acetate (10 mL), and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, and the residue was dissolved in pyridine (15 mL). Acetic anhydride (163 mg) was added thereto, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol), and recrystallized (hexane/ethyl acetate) to give the title compound (201 mg).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in pyridine (15 mL)
  3. additionAcetic anhydride (163 mg) was added
  4. stirringthe mixture was stirred at room temperature for 15 hr
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  7. customrecrystallized (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-727c2cd0ea504d4eaab09ffc38253b34
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729102B2

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