Ethyl Acetate → phosphoric acid di-tert-butyl ester 4-{4-[(2,6-dichloro-benzoylamino)-methyl]-phenyl}-2-oxo-2H-pyridin-1-ylmethyl ester

HRID 1042934

Reaktionsgleichung

Reaktionsgleichung von HRID 1042934
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][N:17]([CH2:20]Cl)[C:16](=[O:22])[CH:15]=2)=[CH:10][CH:9]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].[C:34]([O:38][P:39]([O-:46])([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])([CH3:37])([CH3:36])[CH3:35].[K+].C(OCC)(=O)C>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][N:17]([CH2:20][O:46][P:39](=[O:40])([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])[O:41][C:42]([CH3:43])([CH3:44])[CH3:45])[C:16](=[O:22])[CH:15]=2)=[CH:10][CH:9]=1)=[O:5]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 23674467Potassium di-tert-butyl phosphateHCID 866754212,6-dichloro-N-[4-(1-chloromethyl-2-oxo-1,2-dihydro-pyridin-4-yl)-benzyl]-benzamide

Produkt 1

HCID 71149943phosphoric acid di-tert-butyl ester 4-{4-[(2,6-dichloro-benzoylamino)-methyl]-phenyl}-2-oxo-2H-pyridin-1-ylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2,6-Dichloro-N-[4-(1-chloromethyl-2-oxo-1,2-dihydro-pyridin-4-yl)-benzyl]-benzamide from the previous step was dissolved in 50 mL DMF. Potassium carbonate (1 g) was added followed by potassium di(t-butyl)phosphate (2 g) and tetrabutylammonium iodide (50 mg). The mixture was stirred at 70° C. for four hours after which it was poured into 300 mL ethyl acetate. The organic phase was washed with water and brine, dried with magnesium sulfate and evaporated under vacuum. The crude product was further purified by silica gel chromatography (eluent: ethyl acetate), giving phosphoric acid di-tert-butyl ester 4-{4-[(2,6-dichloro-benzoylamino)-methyl]-phenyl}-2-oxo-2H-pyridin-1-ylmethyl ester as a colorless oil which slowly crystallized.

Aufarbeitung

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried with magnesium sulfate
  3. customevaporated under vacuum
  4. customThe crude product was further purified by silica gel chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e44cac3e8c1145db86fe9fb197a5c8e6
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08558001B2

Verknüpfte Notizen

Wird geladen…