The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Oct. 21, 2003

Filed:

Sep. 20, 2001
Applicant:
Inventors:

Sheryl Davis Debenham, Scotch Plains, NJ (US);

Neil Warren Boaz, Kingsport, TN (US);

Assignee:

Eastman Chemical Company, Kingsport, TN (US);

Attorney:
Primary Examiner:
Assistant Examiner:
Int. Cl.
CPC ...
C07C 6/974 ; C07C 6/104 ;
U.S. Cl.
CPC ...
C07C 6/974 ; C07C 6/104 ;
Abstract

Disclosed are processes for the preparation of enantiomerically-enriched cyclopropylalanine derivatives by the hydrogenation of certain enamides in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst and certain novel enamide ester compounds which are intermediates in the processes. The processes include novel 2-step and 3-step processes for the preparation of enantiomerically-enriched cyclopropylalanine derivatives. The two-step process comprises the steps of reacting cyclopropanecarboxaldehyde with a substituted phosphorylglycine to afford an enamide ester which then is hydrogenated in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst. The three-step process comprises the steps of forming an azlactone from an N-acylglycine and cyclopropanecarboxaldehyde, converting the azlactone to the aforesaid enamide which then is hydrogenated in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst.


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