Water → HCID 67549096, Verbindung

HRID 1425367Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425367
P(=O)(O)(O)O.C(OC([NH:13][CH:14]1[CH2:17][N:16]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)[CH2:15]1)=O)(C)(C)C.C1COCC1.O>ClCCl>[NH2:13][CH:14]1[CH2:17][N:16]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)[CH2:15]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1004Phosphoric Acid2×HCID 8028TetrahydrofuranHCID 67548952Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl)-1,3-benzothiazole-6-carboxylate

Produkt 1

HCID 67549096HCID 67549096, VerbindungAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

85% phosphoric acid (0.23 mL, 1.96 mmol) was added to a solution of ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl)-1,3-benzothiazole-6-carboxylate obtained in Example (225b) (296 mg, 0.78 mmol) in dichloromethane (2 mL) at room temperature, followed by stirring for 27 hours. Then, THF (1 mL) and 85% phosphoric acid (0.23 mL, 1.96 mmol) were added, and the mixture was further stirred for five hours. Water was added to the reaction solution, and the mixture was washed with ethyl acetate. Then, a 1 N aqueous sodium hydroxide solution was added to the aqueous layer, followed by extraction with a chloroform/methanol mixed solvent. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. Thereafter, the solvent was evaporated under reduced pressure to obtain 190 mg of the title compound as a milk white solid (87%).

Aufarbeitung

  1. stirringthe mixture was further stirred for five hours
  2. washthe mixture was washed with ethyl acetate
  3. additionThen, a 1 N aqueous sodium hydroxide solution was added to the aqueous layer
  4. extractionfollowed by extraction with a chloroform/methanol mixed solvent
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThereafter, the solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-27bbc08445cb402989b4cce28642b0fe
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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