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. 2016 Jun 22;59(13):6149–6168. doi: 10.1021/acs.jmedchem.6b00044

Scheme 3.

Scheme 3

Reagents and conditions: (A) (a) TsCl, NEt3, DMAP, CH2Cl2, rt 15 h (88%); (b) LiBr, DMF, rt, 12 h (82%); (c) HBr 48% soln, 80 °C, 20 h (61%); (d) NaN3, H2O, reflux, 12 h (80%); (e) SOCl2, EtOH, 0 °C to rt (78%); (f) K2CO3, DMF (92%); (g) CuSO4 (15 mol %), sodium ascorbate (45 mol %), t-BuOH:H2O:CH2Cl2 (51%); (h) LiOH (aqueous 0.5 M), CH3OH reflux, then HCl (1 M aq), pH 1 (21%). (B) (a) (1) TSTU, N,N-diisopropylethylamine, DMF, (2) LiOH, 0.5 M, MeOH:H2O; (b) TSTU, N,N-diisopropylethylamine, DMF; (c) DMF, water, 0 °C.