4-Cyanobenzoyl isocyanate → t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-cyanobenzoyl)ureido]phenyl]propionate

HRID 1900886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900886
[CH2:1]([S:5]([NH:8][C@@H:9]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[C:25]([C:27]1[CH:37]=[CH:36][C:30]([C:31]([N:33]=[C:34]=[O:35])=[O:32])=[CH:29][CH:28]=1)#[N:26]>C(#N)C>[CH2:1]([S:5]([NH:8][C@@H:9]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:34]([NH:33][C:31](=[O:32])[C:30]2[CH:36]=[CH:37][C:27]([C:25]#[N:26])=[CH:28][CH:29]=2)=[O:35])=[CH:22][CH:23]=1)[C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])(=[O:6])=[O:7])[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 149137394-Cyanobenzoyl isocyanateHCID 57133224t-butyl (2S)-2-(n-butylsulphonylamino)-3-(4-aminophenyl)propionate

Produkt 1

HCID 86749999t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-cyanobenzoyl)ureido]phenyl]propionateAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Example 1, starting material step (c), the product of step (c) (2.59 g) and 4-cyanobenzoyl isocyanate (1.29 g) in acetonitrile (100 ml total) were reacted to give, after stirring at ambient temperature for 1 hour and storage at 10° C. overnight, a solid, which was crystallised from isopropanol to give t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-cyanobenzoyl)ureido]phenyl]propionate (2.32 g) as a white solid: m.p. 171°-173° C.; NMR Spectrum (CDCl3) 0.90 (3H, t), 1.37 (2H, m), 1.49 (9H, s), 1.73 (2H, m), 2.90 (2H, t), 3.11 (2H, m), 4.31 (1H, m), 5.61 (1H, d), 7.19 (2H, d), 7.42 (2H, d), 7.83 (2H, d), 8.19 (2H, d), 9.92 (1H, br s), 10.78 (1H, br s); Mass Spectrum m/Z 529 (M+H)+.

Aufarbeitung

  1. customto give
  2. customstorage at 10° C. overnight, a solid, which was crystallised from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-f372551bc93d4831ab3e78803fe3dce7
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576334

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