Process for the preparation of l-phosphinothricin and its...

Details Process for the preparation of l-phosphinothricin and its... Process for the preparation of l-phosphinothricin and its...

C - Chemistry, Metallurgy

07

F

C07F 9/30 (2006.01) C07F 9/32 (2006.01)

Patent

CA 2085145

HOE 91/F 389 Abstract Process for the preparation of L-phosphinothricin and its derivatives The invention relates to a process for the enantioselec- tive preparation of L-phosphinothricin (L-Ptc) and derivatives of the formula I (I) Image in which R1 is H, (C1-C6)-alkyl, (C1-C4)-haloalkyl, (C3-C6)-cycloalkyl or (subst.) phenyl-(C1-C4)-alkyl, R2 is hydrogen, formyl, [(C1-C6)alkyl]carbonyl, [(C1-C6)alkoxy]- carbonyl, (subst.) benzyloxycarbonyl, (C1-C6)-alkyl- sulfonyl or (subst.) (C6-C10)-arylsulfonyl, and R3 is OH, NH2 or (C1-C6)-alkoxy, or their salts with acids or bases, in which a) an L-vinylglycine derivative II is reacted with a methanephosphonous acid monoester III Image Image (II) (III) in which R4 is defined as R1, excepting H, and R5 is defined as R2, excepting H, and R6 is (C1-C6)alkoxy, in the presence of a catalytic amount of a free radical initia- tor at 70°C to 115°C to give compound Ia of the formula I, in which R1 is defined as R4, R2 is defined as R5 and R3 is defined as R8, and b) if desired the compounds Ia obtained according to step a) are converted by customary hydrolysis and/or aminolysis into structurally different compounds Ib of the formula I, in which R1 is defined as R4 or is H, R2 is defined as R5 or is H and R3 is defined as R6 or is hydroxyl or amino, and c) if desired the compounds Ia or Ib obtained are converted into salts.

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