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. Author manuscript; available in PMC: 2016 May 18.
Published in final edited form as: ACS Chem Neurosci. 2016 Mar 8;7(5):546–552. doi: 10.1021/acschemneuro.5b00345

Scheme 1. Synthesis of Novel Cocaine Haptens Modified at the P3 (Cocaine N-site) Site and Conjugation to the Self-Assembling Peptide Domain KFE8a.

Scheme 1

aReagents and conditions: (a) Saturated NaHCO3 aqueous solution, CH2Cl2, rt, 1 h, 96%; (b) CH3CH(Cl)OCOCl, 1,2-dichloroethane, reflux, 7 h, 91%; (c) MeOH, reflux, 8 h, 90%; (d) BnOCOCH2CH2CH2CH2Br, K2CO3, KI, acetone, 24 h, 73%; (e) H2, Pd–C, MeOH, rt, 12 h, 75%; (f) 20% piperidine in DMF, rt; (g) 4, HBTU, DIEA, HOBt, DIC, DMF, rt, 2.5 h; (h) trifluoroacetic acid/H2O/triisopropylsilane (95%/2.5%/2.5%), rt, 1.5 h.