Process for producing threo-3-amino-2-hydroxybutanoyl-...

C - Chemistry – Metallurgy – 07 – C

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260/508.5, 260/4

C07C 103/85 (1980.01) C07C 129/12 (1980.01)

Patent

CA 1170667

ABSTRACT: A process for producing threo-3-amino-2-hydroxybutanoyl- aminoacetic acids comprises the steps of allowing to react a starting compound represented by the general formula: R1 - ?CH2 - R2 (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: H? - COOR3 (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 R2 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), 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.

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