Process for synthesizing para-and/or meta-substituted cyanophenyalanine derivatives
AssigneeLG Chemical Ltd.
InventorsBong Chan Kim, Sang Yeul Hwang, Jong Chan Lim, Do Hyun Nam, Hyun Ik Shin
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Abstract
The present invention relates to a process for preparing a useful medicinal intermediate represented by the following formula (1): in which, R1, A and n are defined as described in the specification, or its stereoisomer, characterized in that a compound represented by the following formula (2): in which, R, R1, A and n are defined as described in the specification, is reacted with a cyanide in the presence of a nickel catalyst.
Claims17
A process for preparing a compound represented by the following formula 1:
- in which
- R1 represents amino-protecting group,
- A represents i) —OR2 wherein R2 represents hydrogen, lower alkyl, cycloalkyl or phenyl, or ii)
- wherein R3 and R4 independently of one another represent hydrogen, lower alkyl or together with the nitrogen atom to which they are attached represent a heteroalicyclic group,
- n represents an integer of 1 or 2, the —CN or —OR group is located at para or meta position, or its steroisomer, characterized in that a compound represented by the following formula 2:
- in which
- R1, A and n are as defined above, and
- R represents fluorosulfonyl, trifluoromethanesulfonyl or nonafluorobutanesulphonyl, is reacted with a cyanide in the presence of a nickel catalyst.
The process of claim 12 wherein the compound of formula 2 is prepared from D-tyrosine, L-tyrosine, 3,4-dihydroxyphenylalanine, or ester thereof.
A process for preparing a compound represented by the following formula 1 and being produced in an enantiomeric excess of a steroisomer of R configuration or S configuration:
- in which
- R1 represents amino-protecting group,
- A represents i) —OR2 wherein R2 represents hydrogen, lower alkyl cycloalkyl or phenyl, or ii)
- wherein R3 and R4 independently of one another represent hydrogen, lower alkyl or together with the nitrogen atom to which they are attached represent a heteroalicyclic group,
- n represents an integer of 1 or 2, the —CN or —OR group is located at para or meta position, or its steroisomer, characterized in that a compound represented by the following formula 2:
- in which
- R1, A and n are as defined above, and
- R represents fluorosulfonyl, trifluoromethanesulfonyl or nonafluorobutanesulphonyl, is reacted with a cyanide in the presence of a nickel catalyst.
Dependencies are inferred from the claim text.