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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 2.

Scheme 2

Syntheses of 4-Substituted Butyric Acid Pentyl Esters (9, 11, and 12)a

a Reagents: (a) pentanol, DMAP, DMF, rt; (b) BH3–THF complex, THF, −10 °C, N2; (c) 3-chlorophenyl isocyanate, triethylamine, DMF; (d) 3-chlorophenylacetic acid, isobutyl chloroformate, triethylamine, DMF, rt; (e) 4-nitrophenyl chloroformate, triethylamine, DMF, rt; (f) 3-chlorophenol, potassium carbonate, acetonitrile, rt.