Ethyl Acetate → (3-(4-(Hydroxymethyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 1035228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1035228
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.CS(O[CH:15]1[CH2:18][N:17]([C:19]([C:21]2[O:22][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:24][N:25]=2)=[O:20])[CH2:16]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+].C(OCC)(=O)C>CN(C=O)C>[OH:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([S:1][CH:15]2[CH2:16][N:17]([C:19]([C:21]3[O:22][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[N:24][N:25]=3)=[O:20])[CH2:18]2)=[CH:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 4677905(4-Sulfanylphenyl)methanolHCID 580430991-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

Produkt 1

HCID 58043150(3-(4-(Hydroxymethyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanoneAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(4-Mercaptophenyl)methanol (2.38 g, 17.0 mmol) and 53B (5.00 g, 15.5 mmol) were mixed in DMF (80 mL). Cs2CO3 (6.05 g, 18.56 mmol) was added. The mixture was stirred at 90° C. overnight and then cooled room temperature. Ethyl acetate (150 mL) was added and the mixture was washed with water (50 mL). The aqueous layer was extracted with ethyl acetate (100 mL). The organic phases were combined, dried (MgSO4) and evaporated to dryness. The residue was purified by column chromatography eluting with ethyl acetate/heptane (20:80, 40:60 and then 60:40). There was obtained 3.5 g (61%) of 60A as a solid. 1H NMR (500 MHz, CDCl3): δ 4.19 (m, 2H), 4.64 (m, 2H), 4.69 (s, 2H), 5.10 (m, 1H), 7.34 (m, 4H), 7.53 (t, 2H), 7.59 (t, 1H), 8.15 (d, 2H), MS (APCI+) m/z 368 [M−H]+.

Aufarbeitung

  1. temperaturecooled room temperature
  2. washthe mixture was washed with water (50 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (100 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography
  7. washeluting with ethyl acetate/heptane (20:80, 40:60

Quellen und Nachweise

ORD-Eintrag
ord-b3940f7d840c400994f2f480e58dceed
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546375B2

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