5-alkoxy-2(3H)-oxazolone compounds and process for preparing the

Details 5-alkoxy-2(3H)-oxazolone compounds and process for preparing the 5-alkoxy-2(3H)-oxazolone compounds and process for preparing the

1999-05-12

2000-02-01

Ramsuer, Robert W.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

5462714, 548110, 548205, 548214, C07D26344

Patent

active

060204966

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a 5-alkoxy-2(3H)-oxazolone compound and a process for preparing the same.


BACKGROUND ART

The above-mentioned 5-alkoxy-2 (3H) -oxazolone compound can be led to 4-carboalkoxy-2-oxazolidinones which are useful as a synthetic starting material or an intermediate for medicines or agricultural chemicals according to the method described in the following reaction scheme (I): ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 have the same meanings as defined below, and R.sup.4 represents a C.sub.1 to C.sub.15 alkyl group, an alkenyl group, an alkynyl group or an aryl group which may be substituted.
4-Carboalkoxy-2-oxazolidinones can be easily led to .beta.-hydroxy-.alpha.-amino acid which are useful as medical products, medical intermediate or starting materials thereof by hydrolyzing it with an alkali using an aqueous potassium hydroxide solution according to the method described in, for example, Journal of American Chemical Society, vol. 118, pp. 3584-3590 (1996).
As a conventional method for producing 4-carboalkoxy-2-oxazolidinones, the methods as mentioned below may be mentioned.
1: In Journal of Japan Chemical Society, vol. 82, p. 1075 (1961), phosgene is acted on D,L-threonine in the presence of sodium hydroxide, followed by subjecting to esterification with methanol+hydrochloric acid to obtain 5-methyl-4-carbomethoxy-2-oxazoline.
2 In Journal of Japan Chemical Society, vol. 82, p. 1075 (1961), there is described a method in which N-Cbz-D,L-allothoreonine is subjected to ring opening in the presence of sodium hydroxide, followed by esterification of the resulting compound with methanol+hydrochloric acid to obtain 5-methyl-4-carbomethoxy-2-oxazolidinone.
3: In Journal of Organic Chemistry, vol. 44, p. 3967, (1979), there is disclosed that N-carbobenzyloxyglycine ethyl ester is reacted with benzaldehyde in the presence of lithium diisopropylamide to obtain 5-phenyl-4-carbomethoxy-2-oxazolidinone.
4: In Tetrahedron Letters, vol. 29, p. 2069, (1988), there is disclosed a method of obtaining 3-methyl-5-(1-methyl-3-pentenyl)-4-carbomethoxy-2-oxazolidinone by reacting 3-(1-methyl-3-pentenyl)-2,3-epoxy-1-propanol and methyl isocyanate to obtain 4-hydroxymethyloxazolidine and oxidizing it with a chromium compound, and further esterifying the resulting compound with diazomethane.
However, a preparing process which passes through 5-alkoxy-2 (3H) -oxazolone compound has not yet been known as of today.
An object of the present invention is to provide a novel 5-alkoxy-2(3H)-oxazolone compound which is useful as a synthetic starting material or an intermediate of medicines or agricultural chemicals and a process for preparing the same.


DISCLOSURE OF THE INVENTION

The present inventors have investigated to solve the above problems, and as a result, they have found that a novel 5-alkoxy-2(3H)-oxazolone compound which can be obtained easily with a high yield can be used as a synthetic starting material for 4-carboalkoxy-2-oxazolidinones, whereby accomplished the present invention.
That is, the present invention relates to a 5-alkoxy-2(3H)-oxazolone compound represented by the formula (I): ##STR3## wherein R represents a hydrogen atom, a C.sub.1 to C.sub.10 alkyl group which may be substituted, a C.sub.3 to C.sub.10 cycloalkyl group which may be substituted, a C.sub.2 to C.sub.10 alkenyl group which may be substituted or a phenyl group which may be substituted; R.sup.2 represents a hydrogen atom, a C.sub.1 to C.sub.10 alkyl group which may be substituted, a phenyl group which may be substituted or an unsubstituted C.sub.2 to C.sub.10 alkenyl group; and R.sup.3 represents a C.sub.1 to C.sub.10 alkyl group which may be substituted, a C.sub.3 to C.sub.10 cycloalkyl group which may be substituted, a C.sub.2 to C.sub.10 alkenyl group which may be substituted (provided that a 2-alkenyl group is excluded) or a phenyl group which may be substituted.
Moreover, the present invention relates to a process for preparing the 5-alkoxy-2 (3H) -oxazolone compound represented by the above form

REFERENCES:
Reinecke et al Chemical Abstracts, vol. 128, No. 13467, Nov. 17, 99.

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