Triethylamine → Methyl 5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-2-{[(prop-2-en-1-yloxy)-carbamoyl]amino}benzoate

HRID 535451

Reaktionsgleichung

Reaktionsgleichung von HRID 535451
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[N:34]3[C:29]([CH:30]=[CH:31][CH:32]=[CH:33]3)=[C:28]([O:35][CH3:36])[C:27]=2[CH3:37])=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].[CH2:38]([O:41][NH2:42])[CH:39]=[CH2:40].C(N(CC)CC)C>O1CCOCC1.O>[CH3:36][O:35][C:28]1[C:27]([CH3:37])=[C:26]([C:24]([C:21]2[CH:22]=[CH:23][C:14]([NH:13][C:5](=[O:11])[NH:42][O:41][CH2:38][CH:39]=[CH2:40])=[C:15]([CH:20]=2)[C:16]([O:18][CH3:19])=[O:17])=[O:25])[N:34]2[C:29]=1[CH:30]=[CH:31][CH:32]=[CH:33]2

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 420841O-AllylhydroxylamineHCID 66653263Methyl 2-amino-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate

Produkt 1

HCID 86683451Methyl 5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-2-{[(prop-2-en-1-yloxy)-carbamoyl]amino}benzoateAusbeute 160 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

0.251 g (0.83 mmol) of triphosgene diluted in 3 ml of dioxane is added, under an inert atmosphere at ambient temperature, to 0.4 g (1.18 mmol) of methyl 2-amino-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate in 10 ml of dioxane. After stirring for 2.5 hours, 0.267 g (2.36 mmol) of O-prop-2-en-1-ylhydroxylamine and 0.82 ml (5.91 mmol) of triethylamine are added. The reaction medium is stirred for one hour and then hydrolysed with water. The aqueous phase is extracted with dichloromethane. The organic phase obtained is washed with a 1N aqueous solution of hydrochloric acid and a saturated aqueous solution of sodium chloride, and then dried over sodium sulphate, filtered, and concentrated under reduced pressure. 0.581 g of a yellow solid is obtained.

Aufarbeitung

  1. stirringThe reaction medium is stirred for one hour
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. customThe organic phase obtained
  4. washis washed with a 1N aqueous solution of hydrochloric acid
  5. dry with materiala saturated aqueous solution of sodium chloride, and then dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5fbf785230f34dc8baeb183daea3150e
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859544B2

Verknüpfte Notizen

Wird geladen…