Trifluoroacetic acid → N-{[5-(4-amidinophenoxycarbonyl)thiophen-2-yl]methyl}-L-proline methyl ester bis(trifluoroacetate)

HRID 529215

반응식

HRID 529215 반응식
[CH3:1][O:2][C:3](=[O:22])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][C:10]1[S:11][C:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])C)=[O:16])=[CH:13][CH:14]=1.[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].Cl.OC1C=[CH:39][C:35]([C:36]([NH2:38])=[NH:37])=[CH:34]C=1.CCN=C=NCCCN(C)C.Cl>N1C=CC=CC=1>[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].[CH3:1][O:2][C:3](=[O:22])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][C:10]1[S:11][C:12]([C:15]([O:17][C:18]2[CH:20]=[CH:39][C:35]([C:36](=[NH:37])[NH2:38])=[CH:34][CH:21]=2)=[O:16])=[CH:13][CH:14]=1

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 217124Benzenecarboximidamide, 4-hydroxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86714698N-[(5-tert-butoxycarbonylthiophen-2-yl)methyl]-L-proline methyl ester

생성물 2

HCID 6422Trifluoroacetic acid수율 0.1%HCID 86714696N-{[5-(4-amidinophenoxycarbonyl)thiophen-2-yl]methyl}-L-proline methyl ester bis(trifluoroacetate)수율 29%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To the compound (0.55 g, 1.7 mmol) obtained in step 1 was added trifluoroacetic acid (10 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, pyridine (10 ml), 4-hydroxybenzamidine hydrochloride (0.35 g, 2.0 mmol), and WSC hydrochloride (0.48 g, 2.5 mmol) were added to the obtained residue, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by high performance liquid chromatography (water-acetonitrile, each containing 0.1% trifluoroacetic acid) to give the title compound (0.30 g, 0.49 mmol, 29%).

후처리

  1. additionwere added to the obtained residue
  2. stirringthe mixture was stirred at room temperature overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe obtained residue was purified by high performance liquid chromatography (water-acetonitrile

출처 및 근거

ORD 기록
ord-f30eda8940cb4ad9ab51feafb1cafcaf
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346821B2

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