[C:1]([C:4]1[C:5]([O:19][C:20](=[O:22])[CH3:21])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=2)[S:7][CH:8]=1)(=O)[CH3:2].[NH:23]([C:25]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[C:29]([N+:36]([O-:38])=[O:37])[CH:28]=1)=[O:26])[NH2:24].Cl.O>CN(C=O)C>[C:20]([O:19][C:5]1[C:4]([C:1](=[N:24][NH:23][C:25]([C:27]2[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[C:29]([N+:36]([O-:38])=[O:37])[CH:28]=2)=[O:26])[CH3:2])=[CH:8][S:7][C:6]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=1)(=[O:22])[CH3:21]To a solution of acetic acid 4-acetyl-2-(4-tert-butylphenyl)thiophen-3-yl ester (63.3 mg, 0.2 mmol) and 4-hydrazinocarbonyl-2-nitrobenzoic acid (54.0 mg, 0.24 mmol) in DMF (1 mL) was added 12 M aqueous HCl solution (16.7 μL, 0.2 mmol). The reaction mixture was stirred overnight, and then water was added. The precipitated solid was collected by filtration and washed with water and CHCl3 to give product as a pale yellow solid (29.1 mg, yield 28%).
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