Trifluoroacetic acid → (R)-N5-[amino (nitroimino)-methyl]-N-[2-(4-hydroxyphenyl) ethyl]-ornithinamide trifluoroacetate
Reaction equation
[NH2:1][C:2](=[N:28][N+:29]([O-:31])=[O:30])[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:16]([NH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)=[O:17])[NH:8]C(OC(C)(C)C)=O.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>ClCCl>[NH2:1][C:2](=[N:28][N+:29]([O-:31])=[O:30])[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:16]([NH:18][CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)=[O:17])[NH2:8].[F:32][C:33]([F:38])([F:37])[C:34]([O-:36])=[O:35]Participants
Procedure
To a solution of 0.8 g (1.82 mMol) of (R)-N5 -[amino(nitroimino) methyl]-N2 -(tert.-butoxycarbonyl)-N-[2-(4-hydroxyphenyl)ethyl]-ornithinamide in 20 ml of dichloromethane, externally cooled with crushed ice/ethanol, were added 2.5 ml of trifluoroacetic acid, then the mixture was allowed to come up to ambient temperature and stirred for a further 4 hours at this temperature. The clear solution obtained was evaporated down in a water jet vacuum and combined twice with 10 ml of water and once with 10 ml of toluene and then dried once more. The amorphous (R)-N5 -[amino (nitroimino)-methyl]-N-[2-(4-hydroxyphenyl) ethyl]-ornithinamide-trifluoroacetate obtained (0.61 g, 74% of theory), Rf 0.33 (test conditions as in Example 5d) was further processed without any more purification.
Workup
- customto come up to ambient temperature
- customThe clear solution obtained
- customwas evaporated down in a water jet vacuum
- customdried once more
Sources & evidence
- ORD record
- ord-c2a189bfb1134b3a9e8ed777a8f0aac6
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616620
Reaction notes
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