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

HRID 529215

Reaction equation

HRID 529215 reaction equation
[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

Participants

7

Reactant 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

Product 2

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-f30eda8940cb4ad9ab51feafb1cafcaf
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Linked notes

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