Sodium Hydroxide → Pf-06282999

HRID 1056506

Reaktionsgleichung

Reaktionsgleichung von HRID 1056506
[NH2:1][C:2](=[O:21])[CH2:3][NH:4]/[C:5](/[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])=[CH:6]\[C:7]([O:9]CC)=O.C(OCCCC)(=O)C.C[Si]([N:34]=[C:35]=[S:36])(C)C.[OH-].[Na+]>CO.O>[Cl:18][C:16]1[CH:15]=[CH:14][C:13]([O:19][CH3:20])=[C:12]([C:5]2[N:4]([CH2:3][C:2]([NH2:1])=[O:21])[C:35](=[S:36])[NH:34][C:7](=[O:9])[CH:6]=2)[CH:17]=1

Komponenten

6

Edukt 4

HCID 14798Sodium Hydroxide2×HCID 31272Butyl AcetateHCID 75297IsothiocyanatotrimethylsilaneHCID 86684671(Z)-Ethyl 3-((2-amino-2-oxoethyl)amino)-3-(5-chloro-2-methoxyphenyl)acrylate

Produkt 1

HCID 71571306Pf-06282999Ausbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

A reaction vessel equipped with an efficient stirrer was charged with (Z)-ethyl 3-((2-amino-2-oxoethyl)amino)-3-(5-chloro-2-methoxyphenyl)acrylate (15 g, 50.2 mmol), butyl acetate (150 mL) and trimethylsilyl isothiocyanate (160.7 mmole, 21.1 g, 22.7 mL) and the mixture was heated to reflux. After 15 hours, the mixture was cooled to 30° C. and treated with 1N aqueous sodium hydroxide (112.5 mL, 112.5 mmoles). After 30 min, the organic layer was separated and extracted with another portion of 1N sodium hydroxide (37.5 mL, 37.5 mmoles). The combined aqueous phases were extracted twice with dichloromethane (2×45 mL), filtered, and treated with 6N HCl until a pH of 2.5 was achieved. After stirring for 1 hour, the resulting solid was isolated by vacuum filtration, resuspended in 100 mL of a 1:1 methanol-water solution, heated with stirring at 50° C. for 2 hours, and cooled to room temperature before collecting the solid by vacuum filtration, pulling dry and drying in a vacuum oven (20 mm Hg, 50° C.) for 12 hours to afford 8.7 g of the desired product as a tan solid.

Aufarbeitung

  1. customA reaction vessel equipped with an efficient stirrer
  2. temperaturethe mixture was heated to reflux
  3. waitAfter 30 min
  4. customthe organic layer was separated
  5. extractionThe combined aqueous phases were extracted twice with dichloromethane (2×45 mL)
  6. filtrationfiltered
  7. additiontreated with 6N HCl until a pH of 2.5
  8. customthe resulting solid was isolated by vacuum filtration
  9. temperatureheated
  10. stirringwith stirring at 50° C. for 2 hours
  11. temperaturecooled to room temperature
  12. custombefore collecting the solid
  13. filtrationby vacuum filtration
  14. custompulling dry
  15. customdrying in a vacuum oven (20 mm Hg, 50° C.) for 12 hours

Quellen und Nachweise

ORD-Eintrag
ord-34fd90d23fec4a2cbe42bdf0c9f15cea
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399626B2

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