Synthesis, molecular structure, and absolute configuration of an optically active (1-amino-2-phenylethyl) phosphonic acid monohydrate

Abstract

Enantiomers of (1 -amino-2-phenylethyl)phosphonic acid were obtained by resolution of diethyl (1 -amino-2-phenylethy1)phosphonate with dibenzoyl-L-( +)-tartaric acid followed by hydrolysis; X-ray analysis shows S-( +) config u ration for one ena ntio m er.

First Synthesis of (R)‐ and (S)‐1,2,3,4‐Tetrahydroisoquinoline‐3‐phosphonic Acid (TicP) Using a Pictet–Spengler Reaction

“…Additionally, treatment of compound ( R )‐ 8a with a 33 % solution of HBr in acetic acid followed by purification using an ion‐exchange column, afforded ( R )‐phosphophenylalanine 11 in almost quantitative yield. Comparison of the specific optical rotation of ( R )‐ 11 with established data in the literature confirmed the absolute configuration assignments 30…”

ORGANIC PHOSPHORUS COMPOUNDS 96.1RESOLUTION OF 1-AMINO-2-(4-FLUOROPHENYL)ETHYLPHOSPHONIC ACID AS WELL AS SOME DI- AND TRIPEPTIDES

“…. 3 However, in contrast to Kowalik et a1.,3 we also isolated the optically active phosphonate esters and hydrolyzed them to the optically active acids 2a and 2b. The pertinent data are summarized in Scheme I. Peptides containing P-terminal aminophosphonic acids can easily be prepared by coupling N-blocked amino acids or small peptides with free aminoalkane-phosphonic acids or their esters followed by removal of the blocking group^.^ Of the more than fifty coupling procedures known in peptide chemistry only a few of them have been used for phosphonopeptide ~ynthesis.~…”

Optically Active 1-Aminoalkylphosphonic Acids

“…It should be possible to isolate both isomers, and this was achieved in the resolution of diethyl l-amino-2-phenylethylphosphonate 9 with dibenzoyl-L-( +)-tartaric acid in an ethanol methanol mixture. 38 The diastereoisomeric salt that crystallized preferentially had [a]:& = -67.2' (c 1.95, NaOH). It was converted to free ester and hydrolyzed to give the dextro rotatory l-amino-2-phenylethyl phosphonic acid (+)-la.…”