C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
260/472.3, 260/5
C07C 101/30 (1980.01) C07C 125/065 (1980.01)
Patent
CA 1167464
ABSTRACT: A process for producing threo-3 amino-2-hydroxybutanoyl- aminbacetic acids comprises the steps of allowing to react a starting compound represented by the general formula: Image (I), wherein R1 represents a naphthyl or a group of the formula: Image in which R6 and R7 represent individually hydrogen, halogen, amino or a protected amino, hydroxy or a protected hydroxy, a lower alkoxy, a lower alkyl or phenyl and R2 represents a protected amino, with a starting compound represented by the general formula: Image (II), wherein R3 represents hydrogen or an ester residue, to obtain threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its ester represented by the general formula: Image (III), wherein R1, R2 and R3 have the same meanings as above, and then reducing the same into threo-3-protected amino-2-hydroxybutanoic acid or its ester represented by the general formula: Image (IV), wherein R1, R2 and R3 have the same meanings as above, and further converting the above compound into threo -3-amino-2- hydroxybutanoic acid represented by the general formula: Image (V), wherein R? represents amino or a protected amino, thereafter condensing the same, in a conventional manner for forming a peptide bond, with a compound represented by the general formula: Image (VI), wherein R4 represents an alkyl having 3 - 4 carbon atom or 3-guanidinopropyl, while previously protecting as required those groups not relevant to the reaction, and removing the protecting groups for the functional groups to produce threo-3-amino-2- hydroxybutanoylaminoacetic acids represented by the general formula: Image (VII), - 2 - wherein R1 and R4 have the same meanings as above. This inven- tion also provides the compounds represented by the general formula (III) as novel intermediates for the above aimed compounds and a process for producing the intermediates. - 3 -
410051
Aoyagi Takaaki
Nishizawa Rinzo
Saino Tetsushi
Shirai Tadashi
Suzuki Masao
Borden Ladner Gervais Llp
Nippon Kayaku Kabushiki Kaisha
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