ORGANIC PHOSPHORUS COMPOUNDS 99.¹ SYNTHESIS AND PROPERTIES OF N-PHOSPHONOMETHYL-AMINOACETALDEHYDE

Abstract

Interaction of methylene aminoacetaldehyde dimethylacetal and dimethylphosphite produces the phosphonomethyl-substituted aminoacetaldehyde acetal 1. Using bis(trimethylsilyl)phosphite in this reaction and hydrolyzing the reaction mixture with alcohol gives the stable crystalline N-dihydroxyphosphonylmethyl-aminoacetaldehyde acetals 3a and 3b. Complete hydrolysis of 3a and 3b with HCl produces N-dihydroxyphosphonylmethyl-aminoacetaldehyde hydrate, 4, as shown by ¹³C-NMR spectroscopy. None of the compounds exhibited biological activity.

Key Words:

• N-Diethoxyphosphonylmethyl-aminoacetaldehyde dimethylacetal
• N-dihydroxyphosphonylmethyl-aminoacetaldehyde acetals
• N-dihydroxyphosphonylmethyl-aminoacetaldehyde hydrate
• ¹³C-NMR spectra of acetals