Dicyclohexylcarbodiimide → 5-(N-(4-(4-t-Butylphenylsulfonylamino)benzoyl)-phenylalanyl-valylamino)-1,3,4-thiadiazole-2-thione

HRID 1489310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1489310
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:34]=[CH:33][C:18]([C:19]([NH:21][C@H:22]([C:30](O)=[O:31])[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:20])=[CH:17][CH:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:35][C@H:36]([C:40]([OH:42])=O)[CH:37]([CH3:39])[CH3:38].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:68][C:69]1[S:73][C:72](=[S:74])[NH:71][N:70]=1>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:34]=[CH:33][C:18]([C:19]([NH:21][C@H:22]([C:30]([NH:35][C@H:36]([C:40]([NH:68][C:69]3[S:73][C:72](=[S:74])[NH:71][N:70]=3)=[O:42])[CH:37]([CH3:39])[CH3:38])=[O:31])[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:20])=[CH:17][CH:16]=2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 27238472-Amino-5-mercapto-1,3,4-thiadiazoleHCID 22878154(4-(4-t-Butylphenylsulfonylamino)benzoyl)-phenylalanine valine

Produkt 1

HCID 99398845-(N-(4-(4-t-Butylphenylsulfonylamino)benzoyl)-phenylalanyl-valylamino)-1,3,4-thiadiazole-2-thione

Versuchsvorschrift

(4-(4-t-Butylphenylsulfonylamino)benzoyl)-phenylalanine-valine, (0.48 grams) 1-hydroxybenzotriazole (0.15 grams), dicyclohexylcarbodiimide (0.17 grams) and 5-amino-1,3,4-thiadiazole-2-thione (0.5 grams) were reacted according to the procedure described in Example 1. The resulting product was recrystallized from ethanol/pentane to give a white solid. M.P. 140°-144° C. NMR spectrum (d6 -DMSO) 14.1 (s, 1H), 12.6,12.5 (s,s, 1H), 10.8 (s, 1H), 8.6-8.2, 7.8-7.4, 7.4-7.0 (m, 15 H, NM+aromatics), 4.8 (m, 1H), 4.35 (m, 1H), 3.5-2.8 (m, 2H), 2.05 (m, 1H), 1.2 (s, 9H), 0.85 (bs, 6H).

Aufarbeitung

  1. customThe resulting product was recrystallized from ethanol/pentane
  2. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-0830aa79dd4c40b4a0320636638c8e38
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677282

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