N-(Phosphinomethyl)-Aminosäuren uno N-Bis(Phosphinomethyl)-Aminosäuren BZW, Deren Ester

Abstract

Hexahydro-s-triazines of amino acid esters (-CH₂-N[sbnd]A-COOR¹)₃ (A = CH₂, CH₂-CH₂, CH(CH₂)COOMe…; R¹ = Me, Et, i.-Pr) react with phosphonous acid esters RP(O)OR²H (R=Me, Et, i.-Pr, t.-Bu, c-Hex, Ph;R² = Et, Ph) forming tile corresponding N-(phosphinic-methyl)-amino acid esters RP(O)(OEt)-CH₂-NH[sbnd]A-COOR¹ (6–13) and RP(O)(OPh)-CH₂-NH[sbnd]A-COOR¹ (25–34). In case of RP(O)(OEt)H in addition to 6–13 the N-bis(phosphinicmethyl)-amino acid esters 14-17 are obtained too in lower yields, The latter ones 35–42 result with yields of 80–95% only by reactions of RP(OH)₂ end amino acids in the presence of formaldehyde like a modified mannich-reaction. The hydrolysis of 6–13 or 25–34 leads to RP(O)(OH)-CH₂-NH[sbnd]A-COOH and RP(O)(OH)-CH₂-NH[sbnd]A-COOR¹ by various methods.