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

HRID 529215

反応式

HRID 529215 の反応式
[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

参加物

7

反応物 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

生成物 2

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-f30eda8940cb4ad9ab51feafb1cafcaf
出典データセット
uspto-grants-2016_05
特許番号
US09346821B2

関連ノート

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