Sodium Hydroxide → Ethyl 3-allyloxycarbonylamino-3-(3-[3-aminophenylsulphonylamino]-phenyl)-propionate

HRID 968470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968470
[Sn](Cl)Cl.[CH2:4]([O:7][C:8]([NH:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-])=O)[CH:29]=2)(=[O:27])=[O:26])[CH:19]=1)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])[CH:5]=[CH2:6].[OH-].[Na+]>C(O)C>[CH2:4]([O:7][C:8]([NH:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=2)(=[O:27])=[O:26])[CH:19]=1)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])[CH:5]=[CH2:6]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 21101499Ethyl 3-allyloxycarbonylamino-3-(3-[3-nitrophenylsulphonylamino]-phenyl)-propionate

Produkt 1

HCID 21101498Ethyl 3-allyloxycarbonylamino-3-(3-[3-aminophenylsulphonylamino]-phenyl)-propionateAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

43.5 g of tin-(II) chloride were added to a solution of 17.8 g of ethyl 3-{[(allyloxy)-carbonyl]-amino}-3-{{3-{[(3-nitrophenyl)-sulfonyl]-amino}-phenyl}}-propanoate from Example II.2.e in 165 ml of ethanol, and the mixture was heated to reflux for a period of time of 2 h. The reaction mixture was hydrolized with 200 ml of aqueous 2N sodium hydroxide solution, then filtered through silica gel and washed with dichloromethane. The organic phase was dried over magnesium sulphate and concentrated to yield 9.2 g of a solid.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for a period of time of 2 h
  3. filtrationfiltered through silica gel
  4. washwashed with dichloromethane
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-67c4c1bf1eba46ac9556a04389c7aae6
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304037B2

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