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. Author manuscript; available in PMC: 2014 May 29.
Published in final edited form as: Bioorg Med Chem. 2008 Sep 27;17(4):1764–1771. doi: 10.1016/j.bmc.2008.09.058

Scheme 5.

Scheme 5

Reagents and conditions: (a) Boc-Gly-OH, DIC, cat. DMAP, DCM, 100%; (b) i—TMS–acetylene, CuI, Pd(PPh3)2Cl2, Et3N; ii—K2CO3, MeOH, 74%; (c) CuI, Pd(PPh3)2Cl2, 2:1 Et3N/THF, 82%; (d) CuOAc2, DMF, 120 C, 3 days, 66%; (e) H2 (1 atm), Pd/C, MeOH, 92%; (f) RBr, K2CO3, DMF, 100%, 78%; (g) i—1:1 TFA/DCM; ii—BisBocPCH, Et3N, MeOH, 71%, 62%; (h) 1:1 TFA/DCM, 32%, 20%.