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Potassium Iodide → Tert-butyl 2-(2-(benzyloxy)-5-(2-(morpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate

HRID 454651
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 454651
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl.Cl[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[CH2:19]([O:26][C:27]1[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][C:28]=1[C:29]([NH:31][C:32]1[CH:44]=[C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:42]=[CH:41][C:33]=1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C.O.CN(C)C(=O)C>[CH2:19]([O:26][C:27]1[CH:54]=[CH:53][C:52]([O:55][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:51][C:28]=1[C:29]([NH:31][C:32]1[CH:44]=[C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:42]=[CH:41][C:33]=1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 66990772Tert-butyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate

Produkt 1

HCID 66990330Tert-butyl 2-(2-(benzyloxy)-5-(2-(morpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoateAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Potassium carbonate (0.075 g), potassium iodide (0.090 g), and N-(2-chloroethyl)morpholine hydrochloride (0.041 g) were added to an N,N-dimethylacetamide (1.8 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate (0.090 g), followed by stirring at 100° C. for 1 hour. 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 bicarbonate, 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: 80-25% hexane/ethyl acetate] to obtain 0.058 g of tert-butyl 2-(2-(benzyloxy)-5-(2-(morpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate as a light yellow solid.

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 bicarbonate
  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: 80-25% hexane/ethyl acetate]

Quellen und Nachweise

ORD-Eintrag
ord-6ebe1304a662487fb127c7637590dbb0
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492582B2

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