[NH2:1][C:2]1[C:3]([C:18]([O:20]CC)=[O:19])=[N:4][C:5]([CH:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.CO.O.[OH-].[Li+]>C1COCC1.O>[NH2:1][C:2]1[C:3]([C:18]([OH:20])=[O:19])=[N:4][C:5]([CH:8]2[CH2:9][CH2:10][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:16][CH2:17]2)=[CH:6][CH:7]=1Ethyl 3-amino-6-(1,4-dioxaspiro[4.5]dec-8-yl)pyridine-2-carboxylate (Compound 232E, 228 mg, 0.744 mmol) was taken up in THF (1.0 mL) and MeOH (1.0 mL, 25 mmol). This was treated with a solution of Lithium hydroxide, monohydrate (156 mg, 3.72 mmol) in H2O (1.0 mL) and allowed to stir at rt for 4 hours. The THF was removed in vacuo and treated, dropwise with 1N HCl until a pH of ˜5 was achieved. This aqueous solution was extracted with EtOAc (3×50 mL) and saturated with salt and stirred with ˜100 mL DCM. The combined organic layers were dried over Na2SO4, filtered and concentrated to a crude yellow oil which was used without further purification. MS (ES+): m/z=278.86 [MH+]. HPLC: tR=2.39 min (ZQ3, polar—5 min).
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