Synthesis of 2-aryl propenoic acid esters for the production of non-steroidal anti-inflammatory drugs
AssigneeWiSys Technology Foundation, Inc.
InventorM. Mahmun Hossain
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Abstract
A method of producing a compound of the formula: 1 and its pharmaceutically acceptable salts, wherein Ar is a substituted or unsubstituted aromatic or heteroaromatic group; comprising: (1) reacting a compound of the formula: 2 wherein Ar is as described above, with N2CHCOOR, wherein R is alkyl, in the presence of a catalytic amount of a Bronsted acid or Lewis acid to form a compound of the formula: 3 wherein Ar and R are as described above; and (2) reacting the compound of formula (II) with a reducing agent in the presence of an alkyl amine to form a compound of the formula: 4 wherein Ar and R are as described above.
Claims30
A method of producing a compound of the formula:
- 15
- and its pharmaceutically acceptable salts, wherein Ar is a substituted or unsubstituted aromatic or heteroaromatic group;
- comprising:
- (1) reacting a compound of the formula:
- 16
- wherein Ar is as described above, with N2CHCOOR, wherein R is alkyl, in the presence of a catalytic amount of a Bronsted acid or Lewis acid to form a compound of the formula:
- 17
- wherein Ar and R are as described above;
- and
- (2) reacting the compound of formula (II) with a reducing agent in the presence of an alkyl amine to form a compound of the formula:
- 18
- wherein Ar and R are as described above.
A method of producing a compound of the formula:
- 19
- and its pharmaceutically acceptable salts wherein Ar is a substituted or unsubstituted aromatic or heteroaromatic group, comprising reacting a compound of the formula:
- 20
- wherein Ar is as described above and R is alkyl with a reducing agent in the presence of alkyl amine to form a compound of the formula:
- 21
- wherein Ar and R are as described above.
A method of producing a compound of the formula:
- 22
- and its pharmaceutically acceptable salts wherein Ar is a substituted or unsubstituted aromatic or heteroaromatic group comprising reacting a compound of the formula:
- 23
- wherein Ar is as described above, with N2CHCOOR, wherein R is alkyl group in the presence of a catalytic amount of HBF4 to form a compound of the formula:
- 24
- wherein Ar and R are as described above.
A method of producing naproxen and its pharmaceutically acceptable salts comprising:
- (1) reacting an aldehyde of the formula:
- 25
- with N2CHCOOR, wherein R is alkyl, in the presence of a Bronsted acid or a Lewis acid to produce a compound of the formula:
- 26
- wherein R is as described above;
- and
- (2) reacting the compound of formula (VI) with a reducing agent in the presence of an alkyl amine to produce a compound of the formula:
- 27
- wherein R is as described above.
The method of claim 24 wherein the iron Lewis acid is [CpFe(CO)2(THF)]+.
A method of producing naproxen and its pharmaceutically acceptable salts comprising reacting a compound of the formula:
- 28
- wherein R is alkyl with a reducing agent in the presence of an alkyl amine to produce a compound of the formula:
- 29
- wherein R as described above.
The method of claim 26 wherein the reducing agent is BH3.THF.
The method of claim 26 wherein the alkyl amine is a secondary amine.
The method of claim 26 wherein the secondary amine is selected from a group consisting of piperidine and oxazoboralidine and is present in an amount of from about 0.05 to about 0.2 molar equivalents per equivalent of compound (VI).
A method of producing naproxen and its pharmaceutically acceptable salts comprising:
- (1) reacting a compound of the formula:
- 30
- with NH2COOR, wherein R is alkyl, and a catalytic amount of HBF4 to produce a compound of the formula:
- 31
- wherein R is as described above.
Dependencies are inferred from the claim text.