Process for the preparation of cyclic amino acids
OwnerPaolo Rossi, Emilia Vecchioinventors
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Abstract
Amino Acids of formula (1) having high purity, free from the corresponding lactams and chloride anions obtained by reduction of oxyaminoacids of formula (II) 1
Claims10
A process for the preparation of highly pure cyclic amino acids, or the derivatives thereof, of formula (I)
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- wherein:
- R1 and R2, which can be the same or different, are hydrogen, lower alkyl or aryl;
- R3 is OH, NH2 or lower alkoxy;
- n is an integer of 3 to 11,
- which process comprises reducing compounds of formula (IV)
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- wherein
- A=OR;
- R3=OR4 (R4 being C1-C4 alkyl) or NH2;
- R1, R2 and n are as defined in formula (I),
- then hydrolyzing the OR3 group to OH group.
A process for the preparation of cyclic amino acids, or the derivatives thereof, of formula (I)
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- wherein
- R1 and R2, which can be the same or different, are hydrogen, lower alkyl or aryl;
- R3 is OH, NH2 or lower alkoxy;
- n is an integer of 3 to 11,
- which compounds are free from the corresponding lactams and mineral acid anions,
- which process comprises reducing compounds of formula (V)
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- wherein R1, R2 and n have the meanings defined above, in the absence of mineral acids, and the resulting amino acids are purified by simple crystallization from conventional solvents, in the absence of any acid.
A process as claimed in the above claims, wherein R1=R2=H and n ranges from 4 to 7.
A process as claimed in the above claims for the preparation of 1-(aminomethyl)-cyclohexaneacetic acid, 1-(aminomethyl)-cyclooctaneacetic acid, the C1-C4 alkyl esters and the amides thereof.
A process as claimed in any one of the above claims, wherein the compound subjected to reduction is 1-(oxyiminomethyl)-cyclohexaneacetic acid
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1-(Aminomethyl)-cyclohexaneacetic acid free from the corresponding lactam and from inorganic acid ions.
A novel compound selected from the group consisting of:
- 1-(formyl)-cyclohexaneacetic acid;
- ethyl 1-(formyl)-cyclohexaneacetate;
- 1-(oximinomethyl)-cyclohexaneacetic acid;
- ethyl 1-(formyl)-cyclohexaneacetate.
Dependencies are inferred from the claim text.