Potassium Hydroxide → Tert-butyl 2-(4-((5,6-diphenylpyrazin-2-yl)(isopropyl)amino)butoxy)acetate

HRID 1271274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271274
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([N:19]([CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[CH:20]([CH3:22])[CH3:21])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Br[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:35]([O:34][C:32](=[O:33])[CH2:31][O:27][CH2:26][CH2:25][CH2:24][CH2:23][N:19]([C:10]1[CH:9]=[N:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:11]=1)[CH:20]([CH3:21])[CH3:22])([CH3:38])([CH3:37])[CH3:36]

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 79177tert-Butyl bromoacetateHCID 184526554-((5,6-Diphenyl-Pyrazin-2-yl)(isopropyl)amino)butan-1-ol

Produkt 1

HCID 69357196Tert-butyl 2-(4-((5,6-diphenylpyrazin-2-yl)(isopropyl)amino)butoxy)acetateAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

22.84 g of 4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]-1-butanol was dissolved in 160 ml of benzene and 10.73 g of tetra-n-butylammonium hydrogen sulfate and 160 ml of an aqueous 40% potassium hydroxide solution were added. While stirring vigorously under ice cooling, 10.73 g of tert-butyl bromoacetate was added dropwise so as to control the inner temperature within a range from 5 to 10° C. After stirring for 45 minutes, an ice bath was removed and the mixture was stirred at room temperature for one hour. The reaction solution was diluted with water and then extracted with diethyl ether. The extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 21.70 g of the desired compound as a pale yellow oily substance.

Aufarbeitung

  1. customfrom 5 to 10° C
  2. stirringAfter stirring for 45 minutes
  3. customan ice bath was removed
  4. stirringthe mixture was stirred at room temperature for one hour
  5. additionThe reaction solution was diluted with water
  6. extractionextracted with diethyl ether
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4113e19954ae4a85946d395a8cc38d07
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205302B2

Notizen zur Reaktion

Wird geladen…