Benzo(d)thiazol-2-amine → HCID 67711381, Verbindung

HRID 974865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 974865
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([C:23]1(C(O)=O)[NH:28][C:27](=[O:29])[CH:26]([CH2:30][CH:31]([CH3:33])[CH3:32])[N:25]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:24]1=[O:42])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O[N:47]1[C:51](=[O:52])CCC1=O.N[C:55]1[S:56][C:57]2[CH:63]=[CH:62][CH:61]=[CH:60][C:58]=2[N:59]=1>O1CCOCC1.C(OCC)(=O)C>[S:56]1[C:57]2[CH:63]=[CH:62][CH:61]=[CH:60][C:58]=2[N:59]=[C:55]1[C:23]1([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:28]([C:51](=[O:52])[NH2:47])[C:27](=[O:29])[CH:26]([CH2:30][CH:31]([CH3:33])[CH3:32])[N:25]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:24]1=[O:42]

Komponenten

7

Edukt 4

HCID 8706Benzo(d)thiazol-2-amineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 19969579HCID 19969579, Verbindung

Produkt 1

HCID 67711381HCID 67711381, VerbindungAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1.09 g of dicyclohexylcarbodiimide was added to 25 ml of a solution of 2.17 g of (3RS,6SR)-3-benzyl-1-benzyloxy-3-carboxy-6-isobutylpiperazine-2,5-dione and 0.63 g of N-hydroxysuccinimide in anhydrous dioxane. The mixture was stirred at room temperature for 2 hours. Thereto was added 0.80 g of 2-aminobenzothiazole. The mixture was stirred at room temperature for 23 hours. The reaction mixture was diluted with 200 ml of ethyl acetate. The resulting solution was washed with an aqueous solution saturated with sodium hydrogen carbonate and an aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent. The residue was crystallized using ethyl acetate, to obtain 2.77 g of (3RS,6SR)-3-(benzothiazol-2-yl)-carbamoyl-3-benzyl-1-benzyloxy-6-isobutylpiperazine-2,5-dione as a white solid.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 23 hours
  2. washThe resulting solution was washed with an aqueous solution saturated with sodium hydrogen carbonate
  3. dry with materialan aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate
  4. distillationsubjected to distillation
  5. customto remove the solvent
  6. customThe residue was crystallized

Quellen und Nachweise

ORD-Eintrag
ord-0c6600db53ac42138207b9989ff91584
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05607934

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