C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][C@@H:19]([CH3:23])[CH2:18]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:24](I)([CH3:26])[CH3:25]>CC#N.CCOC(C)=O>[CH:24]([N:20]1[CH2:21][CH2:22][N:17]([C:15]([O:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:16])[CH2:18][CH:19]1[CH3:23])([CH3:26])[CH3:25]Potassium carbonate (11.2 g) was added to a solution of (S)-1-benzyloxycarbonyl-3-methylpiperazine (D19)(10.18 g) in CH3CN (60 ml), followed by isopropyl iodide (11.3 ml) and the mixture was heated at reflux overnight. The reaction mixture was then allowed to cool to rt and the inorganics were filtered off. The filtrate was evaporated to give an oil which was taken up in EtOAc (100 ml) and washed with water (2×50 ml). The EtOAc layer was dried (MgSO4) and concentrated to give the title compound (D26) as an oil (8 g). LCMS electrospray (+ve) 277 (MH+).
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