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US 6,806,380 B2Granted
Modified safe and efficient process for the environmentally friendly synthesis of imidoesters
AssigneeLexicon Pharmaceuticals, Inc.
InventorsHartmuth C. Kolb, Ramanaiah C. Kanamarlapudi, Paul F. Richardson, Gaznabi Khan
Life of this patent
Estimating the term…
Abstract
Disclosed is a safe, efficient and environmentally friendly method for preparing imidoesters.
Claims17
A method for preparing imidoesters wherein the imidoester has the formula
- wherein
- R is C1-C10 alkyl or C3-C8 cycloalkyl, each of which is unsubstituted or substituted with one, two, three, four, or five groups independently selected from the group consisting of lower alkyl, lower alkoxy, aryl, arylalkyl, trifluoromethyl, trifluoromethoxy, C3-C8 cycloalkyl, and C3-C8 cycloalkoxy;
- or
- R is aryl, arylalkyl, heteroaryl, and heteroarylalkyl, the ring portion of each is unsubstituted or substituted with one, two, three, four, or five groups independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, aryl, arylalkyl, trifluoromethyl, trifluoromethoxy, C3-C8 cycloalkyl, and C3-C8 cycloalkoxy;
- and
- R′ is alkyl, alkoxyalkyl, cycloalkylalkyl, or
- arylalkyl wherein the aryl group is unsubstituted or substituted with one, two, three, four or five groups independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, aryl, arylalkyl, trifluoromethyl, and trifluoromethoxy, comprising:
- A) treating a nitrile with an anhydrous hydrogen chloride solution and an anhydrous alcohol, and
- B) isolating the imidoester salt.
6 more elements
A method of preparing a compound of the formula:
- wherein
- R is C1-C10 alkyl or C3-C8 cycloalkyl, each of which is unsubstituted or substituted with one, two, three, four, or five groups independently selected from the group consisting of lower alkyl, lower alkoxy, aryl, arylalkyl, trifluoromethyl, trifluoromethoxy, C3-C8 cycloalkyl, and C3-C5 cycloalkoxy;
- or
- R is aryl, arylalkyl, heteroaryl, and heteroarylalkyl, the ring portion of each is unsubstituted or substituted with one, two, three, four, or five groups independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, aryl, arylalkyl, trifluoromethyl, trifluoromethoxy, C3-C8 cycloalkyl, and C3-C8 cycloalkoxy;
- and
- R′ is alkyl, alkoxyalkyl, cycloalkylalkyl, or
- arylalkyl wherein the aryl group is unsubstituted or substituted with one, two, three, four or five groups independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, aryl, arylalkyl, trifluoromethyl, and trifluoromethoxy;
- the method comprising:
- A) reacting a nitrile of the formula
- with an anhydrous hydrogen chloride solution in the presence of at least one
- solvent;
- and
- B) isolating the imidoester salt.
10 more elements
Dependencies are inferred from the claim text.