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Reagents and conditions: (a) BnBr, Cs2CO3, DMF, rt, 12%; (b) 5-(tert-butoxycarbonylamino)-2-chlorobenzoic acid, DIEA, DMF, HBTU, rt to 60 °C, 18%; (c) BnOH, DIAD, PPh3, THF, rt, 24%; (d) Fe, NH4Cl, THF, H2O, 75 °C, 87%; (e) 5-(tert-butoxycarbonylamino)-2-chlorobenzoic acid, DIEA, DCM, T3P, rt, 42%; (f) BnOH, NaH, 0–120 °C, 34%; (g) 5-(tert-butoxycarbonylamino)-2-chlorobenzoic acid, DIEA, DCM, T3P, rt, 26%.
