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and the aqueous layer was washed with CH2Cl2 (25 mL). The or-
ganic layers were combined and concentrated in vacuo. The residue
was purified by MPLC with hexanes as the eluent to obtain a color-
less oil. The compounds prepared by this method were consistent
with those published.
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4.5. General procedure for the esterification of aliphatic acids
2 with DTPP (18)
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DTPP (18)(1.76 g, 5 mmol)was added to analcoholic solution(6 mL)
of the acid (1 mmol), and the reaction mixture was stirred at room
temperature (24 h). The volatiles were removed and the residue was
purified by MPLC with hexanes as the eluent to obtain a colorless oil.
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We thank Mr. Pierre Morieux and Ms. Amber M. King (University
of North Carolina, Chapel Hill) for helpful discussions and advice,
and Professor Michel Gagne (University of North Carolina, Chapel
Hill) for his help in the energy minimization studies. The project
was supported by grant RO1N5054112 (H.K.) from the National
Institute of Neurological Disorders and Stroke.
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Supplementary data
Spectroscopic data (1H and 13C NMR) of all purified products and
experimental details on the use of 18. Supplementary data associ-
ated with this article can be found in the online version, at
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