New phosphonic analogs of aspartic and glutamic acid by aminoalkylation of trivalent phosphorus chlorides with ethyl acetyloacetate or ethyl levulinate and benzyl carbamate

Structure of 5-oxo-2-pyrrolidinylphosphonic acid

“…C-Methyl 4-amino-P,P-diethyl-4-phosphonobutyrate, obtained by the oxime method as 0108-2701/87/020287-03501.50 described by Kowalik, Kupczyk-Subotkowska & Mastalerz (1981) was cyclized by heating at 423 K for 30 min and hydrolysed with 40% solution of hydrobromide in acetic acid at room temperature for 48 h (Oleksyszyn, Gruszecka, Kafarski & Mastalerz, 1982 Pbc21 confirmed by refinement; Syntex P2~ computercontrolled four-circle diffractometer, scintillation counter, graphite monochromator; cell parameters by least squares from setting angles of 15 reflexions with 24 < 20(Mo) < 32 ° measured on diffractometer, 774 independent reflexions; 20max = 55"0°; variable 0--20 scans, scan rate 2.0-29.3 ° min -~ depending on intensity; two standards (235, 433) every 50 reflexions, variation in intensities +3.0%; data corrected for Lorentz-polarization, not for absorption; 748 with 1> 3.0a(/) used for structure determination; index range h0 to 9, k0 to 8, l0 to 16; calculations 5-OXO-2-PYRROLIDINYLPHOSPHONIC ACID performed with Syntex (1976) system; neutral-atom scattering factors from International Tables for X-ray Crystallography (1974); direct methods, Syntex (1976) version of MULTAN (Germain, Main & Woolfson, 1971) (Johnson, 1976) drawing of the title compound with the atom-numbering scheme.…”

Advances in the Chemistry of Aminophosphinic Acids

“…73 p. 538) has recently been successfully extended to include a-aminophosphinic acids such as 53. 64 Instead of using aluminium amalgam, Raney nickel or diborane, respectively, as reducing agents, zinc in formic acid was successful in this case38 and gave yields ranging from 40 to 68%.…”

Aminophosphonic Acids and Aminobis(phosphonic acids) as Potential Inhibitors of Penicillin‐Binding Proteins

“…Oleksyszyn et al encountered the same problem during the synthesis of phosphonic analogues of pyroglutamic acid: in acidic media, the α-methylpyroglutamic acid analogue was in equilibrium with the open-chain compound. [42] Selective deprotection of the phosphonate group of 13 was carried out with trimethylsilyl bromide in dichloromethane followed by treatment with methanol to give compound 16 as a white hygroscopic solid in 90 % yield. The same method was applied to the synthesis of the bis(homologue) (Scheme 6).…”