Figure 3.

Synthesis of the coreceptor inhibitor LJC240−COOH (10). Reagents and conditions: (a) NH₂OH·HCl, NaHCO₃, EtOH/H₂O, rt; (b) Na, pentanol, reflux; (c) (Boc)₂O, TEA, THF, rt; (d) 10% Pd/C, HCO₂NH₄, methanol, reflux; (e) 1-bromo-3-chloropropane, KI, TEA, DMF, rt; (f) 1-acetylpiperidine-4-carboxylic acid, SOCl₂, TEA, DCM, rt; (g) 5, KI, K₂CO₃, MeCN, reflux; (h) HCl, methanol, rt; (i) 4-(chlorosulfonyl)benzoic acid, Na₂CO₃, dioxane/H₂O, rt.