Process for the preparation of oxazoline compound

Details Process for the preparation of oxazoline compound Process for the preparation of oxazoline compound

2000-02-29

2000-10-03

Stockton, Laura L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D26314

Patent

active

061275468

ABSTRACT:
The present invention relates to a process for the preparation of an oxazoline compound which is easily chemically converted to a beta-amino-alpha-hydroxy acid or a gamma-amino-beta-hydroxy acid. The method comprises producing a compound of the following formula (4) using .alpha.-amino acid. The produced compound (4) is subjected to an intramolecular cyclization to produce an oxazoline compound of the following formula (3). The oxazoline compound (3) is oxidized at a vinyl group with RuCl.sub.3 or NaIO.sub.4 to produce an oxazoline compound of the following formula (1) which is easily chemically converted to a beta-amino-alpha-hydroxy acid. Alternatively, the oxazoline compound (3) may also be treated with 9-borabiclo[3.3.1]nonane such that a hydroxy group is introduced into the end of the vinyl group of the oxazoline compound(3). The introduced end hydroxy group is oxidized with RuCl.sub.3 or NaIO.sub.4 to produce an oxazoline compound of the following formula (2) which is easily chemically converted to a gamma-amino-hydroxy acid.

REFERENCES:
Ansari et al., J. Am. Oil Chem. Soc., (1986), 63(7), pp. 908-914, Jul. 1986 .

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