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Sodium Bicarbonate → (2S)-2-{3-[5-(4,5-Dihydro-1,3-oxazol-2-yl)-1H-pyrrol-2-yl]-5-[4-(methyl sulfonyl)phenoxy]phenoxy}propan-1-ol

HRID 1964535
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1964535
C[O:2][CH2:3][C@H:4]([CH3:33])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]3[O:29][CH2:30][CH2:31][N:32]=3)=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1.ClCCl.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[O:29]1[CH2:30][CH2:31][N:32]=[C:28]1[C:26]1[NH:27][C:23]([C:8]2[CH:7]=[C:6]([CH:11]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[CH:9]=2)[O:5][C@@H:4]([CH3:33])[CH2:3][OH:2])=[CH:24][CH:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 580654712-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-4,5-dihydro-1,3-oxazole

Produkt 1

HCID 44178222(2S)-2-{3-[5-(4,5-Dihydro-1,3-oxazol-2-yl)-1H-pyrrol-2-yl]-5-[4-(methyl sulfonyl)phenoxy]phenoxy}propan-1-olAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-4,5-dihydro-1,3-oxazole (3.17 g, 6.74 mmol) synthesized in Example 20 was dissolved in dichloromethane (100 mL), and cooled to −78° C., and a 1.0 mol/l boron tribromide dichloromethane solution (7.07 mL, 7.07 mmol) was added under nitrogen atmosphere. The temperature was raised naturally, followed by stirring at room temperature for 30 minutes, subsequently a saturated aqueous sodium hydrogencarbonate solution was added to neutralize the reaction solution, and extraction was carried out with dichloromethane (200 mL). The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with ethyl acetate (100 mL) and ethanol (50 mL) to afford the desired product (1.96 g, yield 64%) as a white solid.

Aufarbeitung

  1. temperatureThe temperature was raised naturally
  2. extractionthe reaction solution, and extraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialsubsequently dried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. washthe resulting residue was washed with ethyl acetate (100 mL) and ethanol (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-d0f57eb5ee0e4566b4d4ddbbc4b4df30
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08415359B2

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