N,N-bis(2-chloroethyl)-p-toluenesulphonamide → Methyl (2S)-2-{4-[(4-methylphenyl)sulfonyl]-1-piperazinyl}-3-(1-trityl-1H-imidazol-4-yl)propanoate

HRID 497557

Reaktionsgleichung

Reaktionsgleichung von HRID 497557
[NH2:1][C@@H:2]([CH2:7][C:8]1[N:9]=[CH:10][N:11]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=1)[C:3]([O:5][CH3:6])=[O:4].Cl[CH2:33][CH2:34][N:35]([CH2:46][CH2:47]Cl)[S:36]([C:39]1[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=1)(=[O:38])=[O:37]>C(N(C(C)C)CC)(C)C.C(#N)C>[CH3:45][C:42]1[CH:43]=[CH:44][C:39]([S:36]([N:35]2[CH2:34][CH2:33][N:1]([C@@H:2]([CH2:7][C:8]3[N:9]=[CH:10][N:11]([C:13]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:12]=3)[C:3]([O:5][CH3:6])=[O:4])[CH2:47][CH2:46]2)(=[O:38])=[O:37])=[CH:40][CH:41]=1

Komponenten

5

Edukt 2

HCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 7408414H-His(Trt)-OMe

Produkt 1

HCID 60030612Methyl (2S)-2-{4-[(4-methylphenyl)sulfonyl]-1-piperazinyl}-3-(1-trityl-1H-imidazol-4-yl)propanoateAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

A suspension of methyl (2S)-2-amino-3-(1-trityl-1H-imidazol-4-yl)propanoate (1 g, 2.4 mmol) in diisopropylethylamine (5 ml), was stirred at room temperature for 20 minutes. N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide (720 mg, 2.4 mmol) was added and the mixture was stirred at reflux for 3 hours. The mixture was allowed to cool and diluted with acetonitrile. The resultant solution was concentrated under reduced pressure and the residue was suspended in aqueous sodium carbonate solution and extracted with dichloromethane (3×20 ml). The combined organic extracts were washed with brine (3×20 ml), dried (Na2SO4), filtered, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a solvent gradient of dichloromethane:methanol (99:1). The isolated material was dissolved in ether and the resultant solution concentrated under reduced pressure to afford the title compound as a colorless foam, 300 mg, 19% yield.

Aufarbeitung

  1. stirringthe mixture was stirred
  2. temperatureat reflux for 3 hours
  3. temperatureto cool
  4. concentrationThe resultant solution was concentrated under reduced pressure
  5. extractionextracted with dichloromethane (3×20 ml)
  6. washThe combined organic extracts were washed with brine (3×20 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel
  11. washeluting with a solvent gradient of dichloromethane:methanol (99:1)
  12. dissolutionThe isolated material was dissolved in ether
  13. concentrationthe resultant solution concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-eda09d4e0eff4cd9866ba262d47e0e6b
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949577B2

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