[OH-].[Na+].Cl.[C:4](=[NH:20])([NH:9][C:10]1[CH:14]=[CH:13][NH:12][C:11]=1[C:15](OCC)=[O:16])[CH2:5][CH2:6][CH2:7][CH3:8].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C(O)C>[CH2:5]([C:4]1[NH:20][C:15](=[O:16])[C:11]2[NH:12][CH:13]=[CH:14][C:10]=2[N:9]=1)[CH2:6][CH2:7][CH3:8]A solution of sodium hydroxide (1.44 g, 35.9 mmol) in water (7 mL) was added to a solution of ethyl 3-pentanimidamido-1H-pyrrole-2-carboxylate hydrochloride (2.46 g, 8.99 mmol) in ethanol (30 mL). The resultant mixture was heated at reflux for a total of 4 hours. The reaction mixture was cooled to room temperature and the pH adjusted to pH 6.5 with aqueous citric acid. The resultant mixture was extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with saturated aqueous sodium chloride solution, dried (Na2SO4), filtered and evaporated to give the title compound as a pale brown solid (1.69 g).
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