A three-step synthesis of (±)-β-methyleneaspartic acid

A simplified, three‐step synthesis for (±)‐β‐methyleneaspartic acid is described. Condensation of diethyl malonate with ethyl pyruvate gives 1,1,2–tricarbethoxyprop‐1‐ene, which is α‐aminated with chloramine to give 1‐amino‐1,1,2‐tricarbethoxyprop‐2‐ene. The latter is hydrolyzed in acid to give the...

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Veröffentlicht in:	International Journal of Peptide and Protein Research 1984-04, Vol.23 (4), p.420-424
Hauptverfasser:	Hand, Elli Smakula, Baker, David C.
Format:	Artikel
Sprache:	eng
Schlagworte:	(±)-β-methyleneaspartic acid 1,1,2‐tricarbethoxyprop‐1‐ene 1-bromo-1 1‐bromo‐1,1,2,‐tricarbethoxypropane 2-tricarbethoxyprop-1-ene 3-methylene-D 3‐methylene‐D,L‐aspartic acid [71195‐09‐0] Aliphatic compounds Aspartic Acid - analogs & derivatives Aspartic Acid - chemical synthesis beta -methyleneaspartic acid Chemistry chloramine [10599-90-3] Exact sciences and technology glutamate-aspartate transaminase inhibitor L-aspartic acid [71195-09-0] Methods methylaspartate mutase Organic chemistry Preparations and properties tricarbethoxypropane γ-unsaturated amino acids
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Beschreibung
Zusammenfassung:	A simplified, three‐step synthesis for (±)‐β‐methyleneaspartic acid is described. Condensation of diethyl malonate with ethyl pyruvate gives 1,1,2–tricarbethoxyprop‐1‐ene, which is α‐aminated with chloramine to give 1‐amino‐1,1,2‐tricarbethoxyprop‐2‐ene. The latter is hydrolyzed in acid to give the title compound.
ISSN:	0367-8377 1399-3011
DOI:	10.1111/j.1399-3011.1984.tb02740.x