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Reagents and conditions: (a) EDC, HOBt, DIPEA, DMF, 85%; (b) H2, Pd/C, CH3OH, 97%; (c) monomethyladipate, EDC, HOBt, DIPEA, DMF, 100%; (d) TFA, water, 100%; (e) (5-amino-1,3-phenylene)dimethanol, EEDQ, CH3OH, DCM, 36%; (f) methanesulfonic anhydride, Et3N, DCM/DMF, 85%; (g) K2CO3, KI, DMA, 52%; (h) NaBH(OAc)3, DCE, ∼25%; (i) LiOH, THF/water; (j) N-hydroxysuccinimide, EDC, DCM, 26% over two steps.
