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Potassium Carbonate → Methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-(benzyloxy)benzamido)-4-phenylbenzoate

HRID 454695
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 454695
C(=O)([O-])[O-].[K+].[K+].Cl.[NH:8]1[CH2:11][CH2:10][CH2:9]1.CN1CCCC1=O.[CH2:19]([O:26][C:27]1[CH:51]=[CH:50][C:49]([O:52][CH2:53][CH2:54]Br)=[CH:48][C:28]=1[C:29]([NH:31][C:32]1[CH:41]=[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:39]=[CH:38][C:33]=1[C:34]([O:36][CH3:37])=[O:35])=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C.O>[N:8]1([CH2:54][CH2:53][O:52][C:49]2[CH:50]=[CH:51][C:27]([O:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:28]([CH:48]=2)[C:29]([NH:31][C:32]2[CH:41]=[C:40]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:39]=[CH:38][C:33]=2[C:34]([O:36][CH3:37])=[O:35])=[O:30])[CH2:11][CH2:10][CH2:9]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 12308726Azetidine hydrochlorideHCID 66990627Methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate

Produkt 1

HCID 66990372Methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-(benzyloxy)benzamido)-4-phenylbenzoateAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Potassium carbonate (0.15 g) and azetidine hydrochloride (0.046 g) were added to a 1-methyl-2-pyrrolidone (1.3 mL) solution of methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate (0.25 g), followed by stirring at 90° C. for 45 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] to obtain 0.088 g of methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-(benzyloxy)benzamido)-4-phenylbenzoate as a light yellow oily substance.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]

Quellen und Nachweise

ORD-Eintrag
ord-ee6c4b78092441868ea100df8f362ff1
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492582B2

Notizen zur Reaktion

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