C(O)(C(F)(F)F)=O.[O:8]1[C:12]([C:13]([C:20]2[CH:25]=[CH:24][C:23]([O:26]C3CCCCO3)=[CH:22][CH:21]=2)=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:10]=[CH:9]1.C([O-])(O)=O.[Na+]>C(Cl)Cl.[Pd]>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([CH:13]([C:12]2[O:8][CH:9]=[N:10][CH:11]=2)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:21][CH:22]=1TFA (10 mL) was added to a solution of 5.3 (14 mmol) in dry DCM (100 mL) and stirred at room temperature for 2 hours. To the reaction mixture was slowly added solid NaHCO3 with stirring. The reaction was then washed with saturated NaHCO3 (2×), dried over Na2SO4, and concentrated under reduced pressure. The residue was then re-dissolved in EtOH, stirred with Pd—C (1.48 g, 0.7 mmol) under hydrogen at room temperature for 14 hours. The Pd—C was removed by filtration through celite with EtOAc as eluant. After concentration, the residue was chromatographed (silica gel, 1:1 EtOAc/hexane) to afford compound 5.4 (1.3 g, 5 mmol). MS ESI (pos.) m/e 262.1 (M+H).
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