Dicyclohexylcarbodiimide → 5-(N-(9-flourenylmethoxycarbonyl)homophenylalanylamino)-1,3,4-thiadiazole-2-thione

HRID 1489308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1489308
[C:1]([NH:18][C@H:19]([C:27](O)=[O:28])[CH2:20][C:21]1C=CC=CC=1)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].ON1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:55][C:56]1[S:60][C:59](=[S:61])[NH:58][N:57]=1>>[CH:7]1[C:6]2[CH:5]([CH2:4][O:3][C:1]([NH:18][C@H:19]([C:27]([NH:55][C:56]3[S:60][C:59](=[S:61])[NH:58][N:57]=3)=[O:28])[CH2:20][CH2:21][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:2])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 978331Fmoc-phenylalanineHCID 27238472-Amino-5-mercapto-1,3,4-thiadiazole

Produkt 1

HCID 228781335-(N-(9-flourenylmethoxycarbonyl)homophenylalanylamino)-1,3,4-thiadiazole-2-thione

Versuchsvorschrift

Fmoc-phenylalanine (0.8 grams), 1-hydroxybenzotriazole (0.38 grams), dicyclohexylcarbodiimide (0.4 grams) and 5-amino-1,3,4-thiadiazole-2-thione (0.4 grams) were reacted according to the procedure described in Example 1. The resulting product was recrystallized from ethanol/pentane to give a white powder. M.P. 186°-187° C. NMR spectrum (d6 -DMSO) 14.08 (s, 1H), 12.6 (s, 1H), 8.00-7.1 (m, 14 H, NH+aromatics), 4.4-4.1 (m, 4H), 2.8-2.3 (m, 2H), 2.1-1.8 (m, 2H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d874704f291e44af85becda0eaf8e916
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677282

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