(-)-Asparagine → (S)-4-Amino-4-oxo-2-(((quinolin-2-yl)carbonyl)amino)butanoic acid
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.C(Cl)(=O)C(C)(C)C.[NH2:21][C@H:22]([C:27]([OH:29])=[O:28])[CH2:23][C:24](=[O:26])[NH2:25]>C(N(CC)CC)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:21][C@H:22]([C:27]([OH:29])=[O:28])[CH2:23][C:24](=[O:26])[NH2:25])=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Accordingly, the present invention also includes a process for the manufacture of these compounds. Such a process embraces in a first step the manufacture of a mixed anhydride and its conversion into quinargine as described above. The mixed anhydride, e.g. 2,2-dimethylpropionic acid-quinoline-2-carboxylic acid anhydride, can be obtained by adding an adjuvant base, e.g. triethylamine, to a mixture of quinoline-2-carboxylic acid and a reactive acid derivative, preferably pivaloyl chloride. The resulting mixed anhydride is subsequently reacted with asparagine in alkaline solution to give N-(2-quinolylcarbonyl)-L-asparagine. This substance is then converted in a subsequent step with 2-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS, 8aS)-isoquinoline-3(S)carboxamide into N-t-butyl-decahydro-2-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-asparaginyl]-amino]butyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide as described above or optionally into a corresponding salt, preferably the methanesulphonic acid salt, or into an ester.
Sources & evidence
- ORD record
- ord-79fe793399af4ac6b0f2777c87d213c4
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562977B2
Reaction notes
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