C([Li])CCC.[CH2:6]([C:8]1[C:9]([NH:14][C:15](=O)OC(C)(C)C)=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:7].Cl.[OH-].[Na+]>C1COCC1.O.C(OCC)(=O)C.CN(C=O)C>[CH3:7][C:6]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:14][CH:15]=1
Normal-butyllithium (2.69 M, 118.7 mL) was dropwise added to a solution of compound (40a) (32.4 g) in THF (500 mL) at an internal temperature of −30 to −10° C., followed by stirring at 0° C. for 30 min. Subsequently, a solution of DMF (11.18 g) in THF (50 mL) was added to the reaction solution at an internal temperature of −40° C., followed by increasing the temperature to room temperature. Then, 6 N hydrochloric acid (200 mL) was added to the reaction solution, followed by stirring at 60° C. for 2 hr. After cooling, ethyl acetate (200 mL) and water (100 mL) were added to the reaction solution for distribution. The aqueous layer was added to sodium hydroxide (4 M, 300 mL), and pH was adjusted to 12, followed by stirring for 1 hr. The precipitate was collected by filtration, washed by sprinkling water, and dried under reduced pressure to obtain compound (40b) (16.52 g, 86%) as a white solid.
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