Water → HCID 67774815, Verbindung

HRID 1963077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963077
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([N+]([O-])=O)=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[CH3:20].[N+:21]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])#[C-:22].C1CCN2C(=NCCC2)CC1.O>C1COCC1.CC(=O)OCC>[CH2:27]([O:26][C:24]([C:23]1[NH:21][CH:22]=[C:9]([CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[CH3:20])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:25])[CH3:28]

Komponenten

7

Edukt 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 533707Ethyl isocyanoacetateHCID 67773638HCID 67773638, Verbindung

Produkt 1

HCID 67774815HCID 67774815, VerbindungAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The compound of step 3 (21.45 g, 79.07 mmol) and ethyl isocyanoacetate (10.37 ml, 94.88 mmol) were dissolved in 225 ml of anhydrous THF under a nitrogen atmosphere at 5° C. and DBU (14.16 ml, 94.88 mmol) was added dropwise. The solution was stirred at room temperature for 18 h. Then 200 ml of water and 200 ml of EA were added. The organic phase was washed with 1 N hydrochloric acid (200 ml) and brine (150 ml), dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 90:10, then 85:15) to give 16.68 g of the title compound as a yellow solid melting at 120-122° C.

Aufarbeitung

  1. washThe organic phase was washed with 1 N hydrochloric acid (200 ml) and brine (150 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 90:10

Quellen und Nachweise

ORD-Eintrag
ord-7ba9d58585bd4620a8d29bc6c08b9473
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415336B2

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