An improved synthesis of 1-aminophosphonic acids

Preparation of carbon‐14 labelled ampropylfos (1‐[14C]‐α‐aminopropanephosphonic acid)

“…Of the various methods that are available for the preparation of a-aminoalkanephosphonic acids, 4 we have generally found it convenient 5 to use the one-pot procedure described by Oleksyszyn and Tyka,6 based on the interaction of triphenyl phosphite, an aliphatic aldehyde, and ethyl (or benzyl) carbamate in glacial acetic acid, followed by hydrolysis of the first-formed phosphonate ester with hydrochloric acid. The free aminophosphonic acid is then liberated by treatment with propylene oxide.…”

Thioureidoalkylphosphonates in the synthesis of 1-aminoalkylphosphonic acids. The Ptc-aminophosphonate method

“…Modification of the Birum reaction, in which ureas (thiourea) were replaced by Nphenylthiourea (A: Ptc-aminophosphonate method 29,30 and/or by N-benzyl carbamates (C: Zaminophosphonate method, Birum-Oleksyszyn method) 23,25 …”

Brain AT1Angiotensin Receptor Subtype Binding: Importance of Peptidase Inhibition for Identification of Angiotensin II as Its Endogenous Ligand

“…Glutamate phosphonate (4-amino-4-phosphonobutyric acid; GluP) was synthesized in house or by Thesis Chemistry (Mentor, OH). In brief, the in-house procedure was as follows: the GluP precursor ester methyl-3-(ethoxyphosphono)-3-aminopropanoate was synthesized in three steps from readily available ethyl-4-chloro-4-oxobutyrate (Kowalik et al, 1981) and subsequently treated with 9 N HCl under reflux for 20 h. The product was precipitated with methanol/propylene oxide (Oleksyszyn and Tyka, 1977) and recrystallized from ethanol, yielding GluP (Genet et al, 1992). Glutamate thiol was a kind gift from Dr. Sherwin Wilk (Mount Sinai School of Medicine, City University of New York, New York, NY).…”