Sodium Hydroxide → 3-Phenyl-3-(2,4,6-trichlorobenzenesulphonamido)propionic acid

HRID 398326

Reaktionsgleichung

Reaktionsgleichung von HRID 398326
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:17]=1[S:24](Cl)(=[O:26])=[O:25]>O1CCOCC1.O>[C:7]1([CH:2]([NH:1][S:24]([C:17]2[C:18]([Cl:23])=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[Cl:15])(=[O:26])=[O:25])[CH2:3][C:4]([OH:6])=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 14798Sodium Hydroxide2×HCID 69189DL-beta-PhenylalanineHCID 5213352,4,6-Trichlorobenzenesulfonyl chloride

Produkt 1

HCID 230026243-Phenyl-3-(2,4,6-trichlorobenzenesulphonamido)propionic acidAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

1.15 g of 3-amino-3-phenylpropionic acid are dissolved in 25 ml of dioxane and 7 ml of 1N sodium hydroxide and 1.95 g of 2,4,6-trichlorobenzenesulphonyl chloride in 5 ml of dioxane are gradually added, while maintaining the pH at 10.5-11 by addition of 1N sodium hydroxide. After stirring for 2 hours at RT, the mixture is diluted with 100 ml of water, extracted twice with EtOAc and acidified to pH=2 by addition of 6N HCl. The solid formed is drained, washed with water and dried at 40° C. 2.09 g of the expected product are obtained, m.p.−218-219° C.

Aufarbeitung

  1. temperaturewhile maintaining the pH at 10.5-11
  2. extractionextracted twice with EtOAc
  3. additionacidified to pH=2 by addition of 6N HCl
  4. customThe solid formed
  5. washwashed with water
  6. customdried at 40° C

Quellen und Nachweise

ORD-Eintrag
ord-4802316e568349b6a8b39cfad6d851d1
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610882B2

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