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. Author manuscript; available in PMC: 2006 Apr 28.
Published in final edited form as: J Med Chem. 2005 May 19;48(10):3621–3629. doi: 10.1021/jm0500929

Scheme 1.

Scheme 1

Syntheses of 3-Chlorophenyl or Adamantan-1-ylcarbamoylpentanoic Acid Pentyl Ester (7 and 13) and 3-Chlorophenyl- or Adamantan-1-ylacetylaminobutyric Acid Pentyl Ester (8 and 14)a

a Reagents: (a) 3-chloroaniline (for compound 7) or 1-adamantaneamine (for compound 13), EDCI, DMAP, dichloromethane, rt; (b) 1-bromopentane, potassium carbonate, DMF, rt; (c) (1) 3-chlorophenylacetic Acid (for compound 8), 1-adamantaneacetic acid (for compound 14), or 1-adamantanecarboxylic acid (for compound 15), EDCI, DMAP, dichloromethane, rt, (2) 1 N aq NaOH, ethanol, rt.