C(OC([NH:8][CH:9]([CH3:29])[CH:10]([C:12]1([C:25](OC)=[O:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[OH:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+].O(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O>C(Cl)Cl>[OH:11][CH:10]1[C:12]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[C:25](=[O:26])[NH:8][CH:9]1[CH3:29]
To a solution of 1-tert-butyl 4-methyl 4-(2-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)piperidine-1,4-dicarboxylate (8000 mg, 19.2 mmol) in DCM (190 mL) was added TFA (44.4 mL, 576 mmol) at 0° C. and the resulting solution was stirred for 2 h. After removing the volatiles, high vacuum was applied briefly to remove excess TFA, and the residue was dissolved in MeOH (190 mL), and K2CO3 (26.5 g, 192 mmol) was added. The reaction mixture was heated at 60° C. for 2 h. After cooling to room temperature, saturated NaHCO3 solution (60 mL) was added, followed by (BOC)2O (12.6 g, 57.6 mmol). The reaction mixture was stirred overnight, and extracted with DCM. The organic layer was dried with MgSO4, and concentrated to give the crude product, which was purified by column chromatography (0-20% MeOH/DCM, monitored at 210 nM) to give the title compound. LCMS: [(M+1)]+=285
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