[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:15])=[C:6]([CH:14]=1)[C:7]([NH:9][CH2:10][CH:11]=[N:12][OH:13])=[O:8].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.[CH3:37][OH:38].Cl.C([BH3-])#N.[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:15])=[C:6]([CH:14]=1)[C:7]([NH:9][CH2:10][CH2:11][N:12]([CH:37]=[O:38])[OH:13])=[O:8]To a solution of 5-bromo-2-chloro-N-(2-hydroxyimino-ethyl)-benzamide (2 g, 6.9 mmol) in MeOH (75 mL) under an argon atmosphere at 0° C. was added methyl orange (trace) followed by a saturated solution of MeOH/HCl until a persistent red color was observed. Sodium cyanoborohydride (0.52 g, 8.2 mmol) was dissolved in MeOH (10 mL) and was added sequentially with saturated MeOH/HCl over 0.5 h. The reaction mixture was stirred an additional 2 h and the MeOH was removed in vacuo. The residue was basidified with saturated Na2CO3 and extracted (7×25 mL) with dichloromethane/MeOH (9:1). The combined organic extracts were washed with brine, were dried (Na2SO4) and were concentrated to provide the title compound (0.7 g, 35%) as a white solid. ESMS: M+H=293.
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