C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 323/20 (2006.01) C07C 319/20 (2006.01) C07C 323/62 (2006.01)
Patent
CA 2583846
[PROBLEMS] To provide a process for industrially producing 2-amino-2-[2-[4-(3- benzyloxyphenylthio)-2-chlorophenyl]~ethyl]-1,3-propanediol hydrochloride (compound (I)), which is a compound having excellent immunosuppressive activity. [MEANS FOR SOLVING PROBLEMS] The process, which is for producing 2- amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]~ethyl]-1,3-propanediol hydrochloride, is characterized by reacting 4-(3-benzyloxyphenylthio)-2- chlorobenzaldehyde with ethyl diethylphosphonoacetate in a solvent in the presence of a base to obtain ethyl 3-[4-(3-benzyloxyphenylthio)~2- chlorophenyl]acrylate, reducing the ethyl 3-[4-(3-benzyloxyphenylthio)-2- chlorophenyl]acrylate, subjecting the reduced compound to mesylation, iodination, and nitration to yield 1-benzyloxy-3-[3-chloro-4-(3- nitropropyl)~phenylthio]benzene, converting it to 2-[2-[4-(3- benzyloxy~phenylthio)-2-chlorophenyl]ethyl]-2-nitro-1,3-propanediol with formaldehyde, and then reducing it.
La présente invention a pour objet un procédé de synthèse industriel d'hydrochlorure de 2-amino-2-[2-[4-(3-benzyloxyphénylthio)-2-chlorophényl]éthyl]-1,3-propanediol (composé (I)), qui présente une excellente activité immunosuppressive. Ledit procédé implique une réaction entre le 4-(3-benzyloxyphénylthio)-2-chlorobenzaldéhyde et le diéthylphosphonoacétate d~éthyle dans un solvant, en présence d~une base, pour aboutir à la formation de 3-[4-(3-benzyloxyphénylthio)-2-chlorophényl]acrylate d~éthyle, suivie consécutivement de la réduction du 3-[4-(3-benzyloxyphénylthio)-2-chlorophényl]acrylate d~éthyle, de la mésylation, de l~iodation et de la nitration du composé réduit ainsi obtenu pour aboutir au 1-benzyloxy-3-[3-chloro-4-(3-nitropropyl)phénylthio]benzène, de la conversion de ce dernier en 2-[2-[4-(3-benzyloxyphénylthio)-2-chlorophényl]éthyl]-2-nitro-1,3-propanediol à l~aide de formaldéhyde, et enfin de la réduction de ce dernier composé.
Kobayashi Kenichi
Komatsu Hidetaka
Tsubuki Takeshi
Kyorin Pharmaceutical Co. Ltd.
Norton Rose Or S.e.n.c.r.l.,s.r.l./llp
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