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. Author manuscript; available in PMC: 2017 Nov 21.
Published in final edited form as: ChemMedChem. 2016 Oct 24;11(22):2534–2546. doi: 10.1002/cmdc.201600439

Scheme 4.

Scheme 4

Synthesis of Cl-ANT-ANPs derivatives with extended linker. Reagents and conditions: a) pTsOCH2P(O)(OiPr)2, Mg(tBuO)2, DMF, 60°C, 72 h; b) TBAF, THF, RT, 16 h; c) 5-chloroisatoic anhydride, NaH, DMF, 50 °C, 48 h; d) i) MsCl, Py, RT, 2 h; ii) NaN3, DMF, RT, 5 days; iii) H2/Pd/C, MeOH, RT, 14 h; iv) 5-chloroisatoic anhydride, DMF, THF, DMAP, RT, 16 h; e) TMSBr, Py, RT, 12 h, then L-phenylalanine isopropyl ester hydrochloride, TEA, 2,2’-dipyridyldisufide, PPh3, Py, 70 °C, 72 h; f) i) TMSBr, Py, RT, 14 h; ii) morpholine, t-BuOH, DCC, H2O; III) tributylammonium pyrophosphate, DMSO, RT, 48 h.