[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][CH:8]=[N:9][OH:10])=[O:5].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>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]([CH:37]=[O:38])[OH:10])=[O:5]To a solution of 2,5-dichloro-N-(2-hydroxyimino-ethyl)-benzamide (0.72 g, 2.9 mmol) in MeOH (20 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 (0.22 g, 3.5 mmol) was dissolved in MeOH (5 mL) and was added sequentially with saturated MeOH/HCl over 0.5 h. The reaction mixture was stirred an additional 1 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. The residue was purified by flash chromatography (2%-5% MeOH/dichloromethane) to provide the title compound (0.29 g, 40%) as a white solid. 1H NMR (400 MHz, CD3OD): δ 7.53 (s, 1H); 7.44 (s, 2H); 3.56 (t, j=6.2 Hz, 2H); 3.06 (t, j=6.2 Hz, 2H). ESMS: M+H=249.
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