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Phenethylamine → trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-N-(2-phenylethyl)-2,3,4,5-tetrahydro 1,5-benzothiazepine-5-acetamide

HRID 345156
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 345156
N1C2C(=CC=CC=2)C=C1[C:10]([NH:12][C@@H:13]1[C:19](=[O:20])[N:18]([CH2:21][C:22]([OH:24])=O)[C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[S:15][C@H:14]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:11].[C:35]1([CH2:41][CH2:42][NH2:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([N:48]([CH2:53][CH2:54][CH2:55][CH3:56])CCCC)CCC.[I-].ClC1[CH:64]=[CH:63][CH:62]=[CH:61][N+]=1C>C(Cl)(Cl)Cl.ClCCl>[NH:43]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:41]=[C:42]1[C:10]([NH:12][C@@H:13]1[C:19](=[O:20])[N:18]([CH2:21][C:22]([NH:48][CH2:53][CH2:54][C:55]2[CH:56]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[O:24])[C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[S:15][C@H:14]1[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 1001PhenethylamineHCID 7622TributylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 14648568trans-3-(2-Indolecarboxamido)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid

Produkt 1

HCID 14648571trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-N-(2-phenylethyl)-2,3,4,5-tetrahydro 1,5-benzothiazepine-5-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

While a mixture of 2 g of trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid, 20 ml of dichloromethane and 0.2 g of 2-phenylethylamine and tri-n-butylamine is stirred at room temperature, 1.2 g of 2-chloro-N-methylpyridinium iodide is added to the mixture. The mixture is stirred at room temperature for 18 hours. After chloroform is added to the reaction mixture, the mixture is washed with a 5% aqueous solution of hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and a saturated solution of sodium chloride. Thereafter, the mixture is dried, and the solvent is distilled off under reduced pressure. The obtained residue is separated and purified by silica gel column chromatography (eluent: chloroform), and recrystallized from ethanol to give 0.7 g of trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-N-(2-phenylethyl)-2,3,4,5-tetrahydro 1,5-benzothiazepine-5-acetamide 1/2hydrate, m.p. 157°-163° C.

Aufarbeitung

  1. stirringThe mixture is stirred at room temperature for 18 hours
  2. washthe mixture is washed with a 5% aqueous solution of hydrochloric acid
  3. customThereafter, the mixture is dried
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe obtained residue is separated
  6. custompurified by silica gel column chromatography (eluent: chloroform)
  7. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-39b6de57c4af4f87b267fe58e22c2217
Quelldatensatz
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05055464

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