N1C=CC=CC=1.[C:7]([O:11][C:12](=[O:25])[NH:13][C:14]1[O:18][N:17]=[C:16]([C:19]([CH3:24])([CH3:23])[CH2:20][NH:21][CH3:22])[CH:15]=1)([CH3:10])([CH3:9])[CH3:8].[C:26](Cl)(=[O:28])[CH3:27]>C1COCC1>[C:7]([O:11][C:12](=[O:25])[NH:13][C:14]1[O:18][N:17]=[C:16]([C:19]([CH3:24])([CH3:23])[CH2:20][N:21]([C:26](=[O:28])[CH3:27])[CH3:22])[CH:15]=1)([CH3:10])([CH3:9])[CH3:8]Pyridine (0.055 mL, 0.68 mmol) is added to a solution of [3-(1,1-dimethyl-2-methylamino-ethyl)-isoxazol-5-yl]-carbamic acid tert-butyl ester (150.0 mg, 0.59 mmol) in THF (2.0 mL) followed by the addition of acetyl chloride (0.048 mL, 0.68 mmol). The reaction mixture is stirred at room temperature for 3 h. After this time, more pyridine (0.028 mL, 0.34 mmol) and more acetyl chloride (0.024 mL, 0.34 mmol) are added to the reaction mixture and stirred for another 1 h. After this time, the reaction mixture is quenched with saturated aqueous NaHCO3 solution and extracted with ethyl acetate twice. The organic extracts are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using methanol/DCM provides 87.0 mg of the title compound. Yield: 47%. m/z 312 [M+H].
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