Process for the preparation of phosphorus-containing l-amino...

Details Process for the preparation of phosphorus-containing l-amino... Process for the preparation of phosphorus-containing l-amino...

C - Chemistry, Metallurgy

07

F

C07F 9/30 (2006.01) C07C 229/20 (2006.01) C07C 271/22 (2006.01) C07C 311/06 (2006.01) C07C 311/19 (2006.01) C07D 307/16 (2006.01) C07F 9/32 (2006.01) C07F 9/38 (2006.01) C07F 9/655 (2006.01)

Patent

CA 2065128

L-amino acids of the formula I and salts thereof, (see formula I) in which: R1 and R2 independently of each other are hydrogen, (C1-C6) - alkyl, which is unsubstituted or is mono- or polysubstituted by halogen or aryl, or (C3-C10) -cycloalkyl, R3 and R4 independently of each other are hydrogen, (C1-C6) - alkyl, (C2-C6) -alkenyl, (C2-C6) -alkynyl, where the last three radicals mentioned can be straight-chain or branched and can have hetero atoms in the chain, (C1-C6)-alkylcarbonyl, aryl-(C1-C4) -alkylcarbonyl, (C1-C6) -alkoxycarbonyl, (C1-C6) -alkylsulfonyl, benzyl, benzyloxycarbonyl, aryloxycarbonyl or arylsulfonyl, where the last four radicals mentioned are unsubstituted or substituted in the aryl radical, R5 is hydrogen or (C1-C4)-alkyl, which is straight-chain or branched and is unsubstituted or substituted by halogen, aryl or a heterocycle, or (C3-C7)-cycloalkyl and n is 0 or 1, are obtained according to the invention by a) reacting an optically active S-homoserine lactone of the formula II, (see formula II) with hydrogen chloride in the presence of an alcohol of the formula R5-OH to give novel compounds of the formula III, (see formula III) in which R3, R4 and R5 are defined as in formula I, except that R5 = H, and b) reacting the resulting compound of formula III with a compound of formula IV, R1(O)n - R(OR2)2 (IV) and if desired, hydrolyzing the product to give a compound of formula I, in which R5 = H.

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