[OH:1][CH:2]([CH2:26][CH3:27])[C:3](=[N:19][NH:20][C:21](OCC)=[O:22])[N:4]1[CH2:9][CH2:8][C:7]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:12][C:6]=2[CH2:5]1.[Na].Cl>CCO>[CH2:26]([CH:2]1[O:1][C:21](=[O:22])[NH:20][N:19]=[C:3]1[N:4]1[CH2:9][CH2:8][C:7]2[N:10]=[C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[O:12][C:6]=2[CH2:5]1)[CH3:27]330.00 mg (576 μmol) ethyl N′-[2-hydroxy-1-(2-phenyl-6,7-dihydro-4H-oxazolo[5,4-c]pyridin-5-yl) butylidene]-hydrazinecarboxylate are placed in 10 mL EtOH, a solution of 280.00 mg (12.17 mmol) sodium in 10 mL EtOH is added and the mixture is stirred overnight at RT. The reaction mixture is adjusted to pH 5-6 with ethanolic HCl and the solvent is eliminated in vacuo. The residue is extracted with EA and H2O, the organic phase is dried and the solvent is eliminated in vacuo. The residue is purified on silica gel. (Eluant: cyclohexane/EA).
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