Cesium carbonate → HCID 58043105, Verbindung

HRID 1035219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1035219
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:10])[CH:3]=1.CS(O[CH:16]1[CH2:19][N:18]([C:20]([C:22]2[O:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:25][N:26]=2)=[O:21])[CH2:17]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl>[CH3:10][C:4]1[CH:3]=[C:2]([O:1][CH:16]2[CH2:17][N:18]([C:20]([C:22]3[O:23][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[N:25][N:26]=3)=[O:21])[CH2:19]2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 4581854-Hydroxy-2-methylbenzaldehydeHCID 580430991-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

Produkt 1

HCID 58043105HCID 58043105, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 4-hydroxy-2-methylbenzaldehyde (0.11 g, 0.79 mmol) and 53B (0.20 g, 0.62 mmol) in DMF (10 mL) under nitrogen was added Cs2CO3 (0.24 g, 0.74 mmol). The mixture was stirred at 90° C. for 20 h, cooled to RT and then diluted with DCM. The solids were filtered off and the filtrate was evaporated. The product was purified on two occasions by preparative HPLC (Kromasil, C8) eluting with a gradient of acetonitrile and a mixture of acetic acid and water (0.2%). The pure fractions were iii combined and concentrated. The aqueous residues were extracted with DCM and the organic solutions were evaporated. There was obtained 162 mg (72%) of 53C as a solid. 1H NMR (500 MHz, CDCl3): δ 2.66 (s, 3H), 4.34 (d, 1H), 4.69 (dd, 1H), 4.76 (d, 1H), 5.17 (m, 2H), 6.64 (d, 1H), 6.72 (dd, 1H), 7.53 (t, 2H), 7.59 (t, 1H), 7.78 (d, 1H), 8.15 (d, 1H), 10.14 (s, 1H), MS (APCI+) m/z 364 [M+H]+.

Aufarbeitung

  1. temperaturecooled to RT
  2. filtrationThe solids were filtered off
  3. customthe filtrate was evaporated
  4. customThe product was purified on two occasions by preparative HPLC (Kromasil, C8)
  5. washeluting with a gradient of acetonitrile
  6. additiona mixture of acetic acid and water (0.2%)
  7. concentrationconcentrated
  8. extractionThe aqueous residues were extracted with DCM
  9. customthe organic solutions were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1ec62a60376b40079f3a98e9bd0df5be
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546375B2

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