Preparation of glutaric acid derivatives
The Invention provides a process for preparing a compound of the formula: ##STR1## or a base salt thereof, wherein R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl optionally substituted by up to 3 substituents each independently selected from the group consisting of C.sub.1 -C.sub.6 alkoxy and C.sub.1 -C.sub.6 alkoxy(C.sub.1 -C.sub.6 alkoxy)-; and R.sup.3 is C.sub.1 -C.sub.6 alkyl or benzyl, said benzyl group being optionally ring-substituted by up to 2 nitro or C.sub.1 -C.sub.4 alkoxy substituents comprising reacting a compound of the formula: ##STR2## wherein R.sup.1 is C.sub.1 -C.sub.4 alkyl, phenyl or benzyl or C.sub.1 -C.sub.4 alkoxy; and R.sup.2 and R.sup.3 are as previously defined for a compound of the formula (I), with hydrogen peroxide or a source of peroxide ions: said process being optionally followed by conversion of the compound of the formula (I) to a base salt thereof. The present invention also relates to novel compounds of the formula (II).
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Claims
1. A process for preparing a compound of the formula: ##STR6## or a base salt thereof, wherein R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl optionally substituted by up to 3 substituents each independently selected from the group consisting of C.sub.1 -C.sub.6 alkoxy and C.sub.1 -C.sub.6 alkoxy (C.sub.1 -C.sub.6 alkoxy)-; and R.sup.3 is C.sub.1 -C.sub.6 alkyl or benzyl, said benzyl group being optionally ring-substituted by up to 2 nitro or C.sub.1 -C.sub.4 alkoxy substituents,
- comprising: reacting a compound of the formula: ##STR7## wherein R.sup.1 is C.sub.1 -C.sub.4 alkyl, phenyl, benzyl or C.sub.1 -C.sub.4 alkoxy; and R.sup.2 and R.sup.3 are as previously defined for a compound of the formula (I), with peroxide ions.
2. The process of claim 1, further including conversion of the compound of formula (I) to a base salt thereof.
3. The process of claim 1 in which the source of the peroxide ions is hydrogen peroxide, a peroxy(C.sub.1 -C.sub.4) alkanoic acid, sodium perborate or a hydrate thereof, or sodium percarbonate, and in which water is present in said reacting step.
4. The process of claim 1 in which the source of the peroxide ions is hydrogen peroxide and in which water is present in said reacting step.
5. The process of claim 1 wherein said reacting step is carried out in a suitable solvent and in the presence of an acid.
6. The process of claim 1 wherein said reacting step is carried out in a suitable solvent and in the presence of a base.
7. The process of claim 5 wherein the solvent is tert-butanol.
8. The process of claim 5 wherein the acid is a mineral acid.
9. The process of claim 8 wherein the mineral acid is sulphuric acid.
10. The process of claim 1 wherein said reacting step is carried out in acetic acid.
11. The process of claim 6 wherein the base is selected from the group consisting of sodium hydroxide, sodium carbonate, sodium bicarbonate, potassium hydroxide, potassium carbonate, and potassium bicarbonate.
12. The process of claim 11 wherein the base is selected from the group consisting of sodium bicarbonate and potassium bicarbonate.
13. The process of claim 1 wherein R.sup.1 is C.sub.1 -C.sub.4 alkyl, phenyl or C.sub.1 -C.sub.4 alkoxy; R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl optionally substituted by one C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 alkoxy (C.sub.1 -C.sub.6 alkoxy)- substituent; and R.sup.3 is C.sub.1 -C.sub.6 alkyl or benzyl, said benzyl group being optionally ring-substituted by one nitro or C.sub.1 -C.sub.4 alkoxy substituted.
14. The of claim 13 wherein R.sup.1 is methyl, phenyl or oxy; R.sup.2 is hydrogen, 2-methoxyethoxymethyl, 2-methoxyethyl or methoxymethyl; and R.sup.3 is ethyl, tert-butyl, benzyl, 4-nitrobenzyl or 4-methoxybenzyl.
15. The process of claim 13 wherein R.sup.1 is methyl or ethoxy; R.sup.2 is hydrogen or 2-methoxyethoxymethyl; and R.sup.3 is tert-butyl.
16. A process for preparing a compound of the formula: ##STR8## wherein R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl optionally substituted by up to 3 substituents each independently selected from the group consisting of C.sub.1 -C.sub.6 alkoxy and C.sub.1 -C.sub.6 alkoxy(C.sub.1 -C.sub.6 alkoxy)-; and R.sup.3 is C.sub.1 -C.sub.6 alkyl or benzyl, said benzyl group being optionally ring-substituted by up to 2 nitro or C.sub.1 -C.sub.4 alkoxy substituents, comprising: reacting a compound of the formula: ##STR9## wherein R.sup.1 is C.sub.1 -C.sub.4 alkyl, phenyl or benzyl; and R.sup.2 and R.sup.3 are as defined for the formula (I), with a source of peroxide ions under acidic conditions.
| 274234 | July 1988 | EPX |
- Allinger, "Organic Chemistry," p. 524, 1974. Payne, J. Org. Chem., vol. 24, pp. 4793-4797, 1961. Zavialov, Tetrahedron, vol. 20, pp. 2745-2750, 1964. Middeton, Aust. J. Chem., vol. 33, pp. 2467-2476, 1980. Mannich, Ber., 74, 1007 (1941).
Type: Grant
Filed: May 15, 1997
Date of Patent: Jul 28, 1998
Assignee: Pfizer Inc. (New York, NY)
Inventor: Stephen Challenger (Kingsdown)
Primary Examiner: Michael L. Shippen
Attorneys: Peter C. Richardson, Paul H. Ginsburg, Grover F. Fuller, Jr.
Application Number: 8/856,612
International Classification: C07C 6974;
