| dc.description.abstract | This investigation was aimed at the synthesis of
two new potential protecting groups for the carboxamide
side chain of the asparagine and glutamine. A
comparative study of preparations of p-nitrophenyl and
N-hydroxysuccinimido tert-Butyloxycarbonyl amino acid
esters was carried out.
The synthesis of 4-methoxy~-methylbenzylamine
and 3-methylbenzhydrylamine precursors for the carboxamide
protecting groups was attempted. The 4-methoxy-
2-methylaniline was diazotized and Sandmeyer reaction
was utilized to obtain 4-methoxy-Z-methylbenzonitrile.
This nitrile was reduced with lithium aluminium hydride
to give 4-methoxy-Z-methylbenzylamine. The synthesis
of m-bromotoluen was carried out by acetylating ptoluidine,
followed by bromination and the removal of ,:
the acetyl group by hydrolysis, diazotization, and
replacement o£-NZ with hydrogen. Grignard reagent,
3-methylphenyl magnesium bromide, was prepared in
anhydrous ether solution from. magnesium turnings and
the m-bromotoluene. The 3-mehylpnenyl magnesium
bromide was coupled with benzonitrile followed by acid
hydrolysis to give 3-methylbenzophenone. The synthesis
of 3-methylbenzhydrylamine from the 3-methylbenzophenone
by the Leuckart reaction was unsuccessful | en |
