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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
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HRID 345156 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매

2
HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-39b6de57c4af4f87b267fe58e22c2217
출처 데이터셋
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05055464

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