[OH:1][CH2:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(OCC)(=O)C>O1CCCC1.[Cl-].[Na+].O>[CH3:28][S:29]([O:1][CH2:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][CH2:8][NH:9][C:10]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:16])=[CH:5][CH:4]=1)(=[O:31])=[O:30]A solution of tert-butyl 4-(hydroxymethyl)phenethylcarbamate (2.51 g, 9.99 mmol) and N,N-diisopropylethylamine (1.9 mL, 11 mmol) in tetrahydrofuran (50 mL) was stirred and cooled in an ice bath. Methanesulfonyl chloride (0.85 mL, 11 mmol) was added in several portions, and stirring was continued in the bath for 50 minutes. The reaction mixture was transferred to a separatory funnel containing ethyl acetate (200 mL) and brine (200 mL). The organic layer was dried over sodium sulfate and concentrated to afford 4-(2-(tert-butoxycarbonylamino)ethyl)benzyl methanesulfonate as a soft white solid. (3.29 g, 100% yield).
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