[OH:1][CH2:2][C:3]1[N:8]=[C:7]([O:9][CH2:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:6]=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].O>C(Cl)Cl>[CH3:33][S:34]([O:1][CH2:2][C:3]1[N:8]=[C:7]([O:9][CH2:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:6]=[CH:5][CH:4]=1)(=[O:36])=[O:35]tert-Butyl (2S)-2-({[6-(hydroxymethyl)pyridin-2-yl]oxy}methyl)piperidine-1-carboxylate (520 mg, 1.61 mmol) and DIPEA (0.842 ml, 4.84 mmol) dissolved in DCM (10 ml) was cooled using an ice bath. Methanesulfonyl chloride (0.191 ml, 2.419 mmol) was added and the reaction stirred for 2 h. DCM (150 ml) and water (150 ml) were added and the phases separated. The organic phase washed with water (150 ml), dried through a phase separator and evaporated in vacuo, yielding the title compound as a light yellow oil (672 mg (104%)) which was used directly in the next step without further purification. MS (ESI+) 401.20 (M+1H+)
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