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US 8,524,943 B2Granted
Production of trans-4-aminocyclopent-2-ene-1-carboxylic acid derivatives
AssigneeDr. Reddy's Laboratories, Inc.
InventorsRichard Lloyd, Justine Ann Peterson, Mark Jackson
Life of this patent
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Abstract
Methods of producing compositions of trans-4-amino-2-cyclopentene-1-carboxylic acid derivatives are described. Also described is an amine salt of a compound having formula A, having components present in both cis and trans structures.
Claims23
A process for preparing trans-4-amino-2-cyclopentene-1-carboxylic acid derivatives represented by formula 1, comprising:
- a) providing a composition comprising a compound of formula A,
- having components present in both cis- and trans-structures, wherein R1 is an alkyl or aryl group having up to 12 carbon atoms, in a solvent;
- b) combining with an amine to form salts, wherein some salt precipitates but the salt of a trans-structure of compound A remains in the solution in excess of the amount of the salt of the cis-structure of compound A remaining in the solution;
- c) separating the precipitate from the solution;
- d) adding acid to the solution to re-form carboxylic acids from the salts in the solution;
- e) isolating the compound 1, which is the trans-structure of compound A;
- and
- f) optionally, purifying the composition from e) to produce a diastereomeric excess of the trans-structure of compound A.
5 more elements
A compound which is an amine salt of a compound having formula A,
- having components present in both cis and trans structures, wherein R1 is an alkyl or aryl group having up to 12 carbon atoms and
- wherein the salt-forming amine has the formula NR1R2R3, where:
- R1 is benzyl, or a non-cyclic alkyl or alkenyl group of 3 to 10 carbon atoms;
- R2 is benzyl, an alkyl group of about 1 to 10 carbon atoms, an alkenyl group of about 3 to 10 carbon atoms, an alkylamino of up to three carbon atoms, or hydrogen;
- and R3 is benzyl, an alkyl group of about 1 to 10 carbon atoms, an alkenyl of about 3 to 10 carbon atoms, an alkylamino of up to three carbon atoms, or hydrogen;
- provided that R1 and R2 cannot both be alkyl groups of four or fewer carbon atoms when R3 is hydrogen.
3 more elements
Dependencies are inferred from the claim text.