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. Author manuscript; available in PMC: 2011 Apr 22.
Published in final edited form as: J Med Chem. 2010 Apr 22;53(8):3198–3213. doi: 10.1021/jm901839g

Scheme 6.

Scheme 6

Reagents and conditions: a: i) (Boc)2O, TEA, DCM, r.t., 2 h; ii) MeOH, EDCI, HOBt, TEA, DMAP, DCM, 10 h;

b: NaBH4, MeOH, THF, reflux, 4 h;

c: I2, PPh3, imidazole, DCM, 0 °C-rt, 2 h;

d: Troc-L-Cys-OMe, TEA, DMF, 85 °C, 2 h;

e: i) TFA, r.t., 30 min; ii) C15H31COOH, EDCI, HOBt, TEA, DMAP, DMF, 60 °C, 10 h;

f: i) Zn dust, AcOH, H2O, THF, r.t., 1 h; ii) (Boc)2O, TEA, DCM, r.t., 1 h;

g: i) Ba(OH)2, THF/H2O, 60 °C, 1 h; ii) H-L-Ser(tBu)-OMe•HCl, EDCI, HOBt, EDIPA, DMAP, DMF, 60 °C, 10 h;

h: TFA, r.t., 30 min.