3-Nitrobenzenesulfonyl chloride → Ethyl 3-allyloxycarbonylamino-3-(3-[3-nitrophenylsulphonylamino]-phenyl)-propionate

HRID 968469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968469
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:14]([O:17][C:18]([NH:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=1)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:19])[CH:15]=[CH2:16]>N1C=CC=CC=1>[CH2:14]([O:17][C:18]([NH:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][S:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)(=[O:12])=[O:11])[CH:29]=1)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:19])[CH:15]=[CH2:16]

Komponenten

4

Edukt 2

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 21101501Ethyl 3-allyloxycarbonylamino-3-(3-aminophenyl)-propionate

Produkt 1

HCID 21101499Ethyl 3-allyloxycarbonylamino-3-(3-[3-nitrophenylsulphonylamino]-phenyl)-propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

3-Nitrophenylsulphonyl chloride was added at 0° C. to a solution of 11.6 g ethyl 3-{[(allyloxy)-carbonyl]-amino}-3-(3-aminophenyl)-propanoate from Example II.2.d in 110 ml of pyridine. After a reaction time of 2 h, the mixture was concentrated, 1 N hydrochloric acid was added, and the solution was extracted with dichloromethane. After drying the organic phase over magnesium sulphate, the solvent was removed and the crude product was purified by chromatography on silica gel (dichloromethane/methanol=40:1) to give 17.8 g of a solid.

Aufarbeitung

  1. concentrationAfter a reaction time of 2 h, the mixture was concentrated
  2. addition1 N hydrochloric acid was added
  3. extractionthe solution was extracted with dichloromethane
  4. dry with materialAfter drying the organic phase over magnesium sulphate
  5. customthe solvent was removed
  6. customthe crude product was purified by chromatography on silica gel (dichloromethane/methanol=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-28c86e642fa344579c18ed5d1971b588
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304037B2

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