Hydrochloric Acid → 2-[N-(4-amidinophenyl)aminomethyl]benzothiazole-5-carboxylic acid-N-phenvl-N-(2-carboxyethyl)amide
Reaction equation
[C:1]1([N:7]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[C:8]([C:10]2[CH:11]=[CH:12][C:13]3[S:17][C:16]([CH2:18][NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26](=[NH:28])[NH2:27])=[CH:22][CH:21]=4)=[N:15][C:14]=3[CH:29]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C(O)C>[C:1]1([N:7]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[C:8]([C:10]2[CH:11]=[CH:12][C:13]3[S:17][C:16]([CH2:18][NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26](=[NH:27])[NH2:28])=[CH:22][CH:21]=4)=[N:15][C:14]=3[CH:29]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
0.45 g (0.84 mMol) of 2-[N-(4-amidinophenyl)-aminomethyl]-benzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide were dissolved in 15 ml of ethanol, mixed with 2 ml of 2N sodium hydroxide solution and stirred for 4 hours at room temperature. Then the mixture was acidified with 3 ml of 2N hydrochloric acid and the solvent was distilled off. The crude product obtained was taken up in 5 ml dichloromethane/ethanol (2:1) and filtered to remove the insoluble sodium chloride. After the distillation of the solvent the desired compound was obtained as a yellow foam. Yield: 0.26 g (67% of theory), Rf value: 0.47 (silica gel; methanol/5% aqueous sodium chloride=6:4) C25H23N5O3S (473.55) Mass spectrum: (M+H)+ =474
Workup
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-4d5fa5a0cc27444db5260137e6a93640
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06087380
Reaction notes
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