[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>[C:15]([N:7]1[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3][C@@H:2]1[CH3:1])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1(S)-tert-butyl 3-methylpiperazine-1-carboxylate (6.00 g, 30.0 mmol) was dissolved in dry DMF (40 mL) and N,N-diisopropylethylamine (DIEA) (6.00 mL). Benzoyl chloride (3.65 mL, 31.5 mmol) was added drop-wise and the reaction was stirred at rt for 16 hours. The reaction was taken up in ethyl acetate (200 mL) and washed with aqueous K2CO3 (10%), water, and saturated sodium chloride. The organic phase was dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-50% ethyl acetate gave an off-white solid.
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