Trifluoroacetic acid → HCID 178512674, compound

HRID 2289740Notes

Reaction equation

HRID 2289740 reaction equation
C([O:5][C:6](=[O:34])[C@H:7]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[NH:8][S:9]([C:12]1[CH:21]=[C:20]2[C:15]([C:16]([Cl:26])=[CH:17][N:18]=[C:19]2[NH:22][C:23]([NH2:25])=[NH:24])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(C)(C)C.[C:35]([C:39]([OH:41])=[O:40])([F:38])([F:37])[F:36]>C(Cl)Cl.C1(C)C=CC=CC=1>[F:36][C:35]([F:38])([F:37])[C:39]([OH:41])=[O:40].[Cl:26][C:16]1[C:15]2[C:20](=[CH:21][C:12]([S:9]([NH:8][C@H:7]([C:6]([OH:34])=[O:5])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:10])=[O:11])=[CH:13][CH:14]=2)[C:19]([NH:22][C:23]([NH2:25])=[NH:24])=[N:18][CH:17]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451189HCID 178451189, compound

Product 1

HCID 178512674HCID 178512674, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-phenylalanine t-butyl ester (30 mg, 0.060 mmol) was dissolved in CF3CO2H (2.5 mL) and the mixture stirred at room temperature for 2.5 h. The mixture was diluted with CH2Cl2 and PhMe, concentrated in vacuo, azeotroping with PhMe, and the residue triturated with Et2O to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-phenylalanine trifluoroacetate (24.4 mg, 0.42 mmol) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customazeotroping with PhMe
  3. customthe residue triturated with Et2O

Sources & evidence

ORD record
ord-fb3eaa5b36f14e7899f3d03c4511fb3b
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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