Über d , l ‐β‐[Furyl‐2]‐α‐alanin

Synthesis of 14C‐labelled heterocyclic analogues of phenylalanine with pyrazole and furan rings

“…The yield of white crystalline DL-3-( l'-pyra~olyl)-alanine-2-~~C (I) was 74 mg (30 %) ; spec. DL-3-(3'-Pyra~olyl)-aIanine-2-~~C (11). Sodium (94 mg; 4.1 mg-atom) was dissolved in absolute ethanol (fi ml) and the solution treated with diethyl a~etamidornalonate-2-~~C (434 mg; 2 mmoles) with specific radioactivity 50 pCi/mmole (2.3 pCi/mg).…”

“…This work was directed to synthesis of further potential 14C-labelled analogues of phenyl-alanine, bearing an unchanged a-alanine side chain, but with the benzene nucleus replaced by another aromatic system. From a number of such compounds, DL-3-( 1'-pyrazoly1)-alanine (I), DL-3-(3'-pyrazolyl)-alanine (11) and DL-3-(2'-furyl)-alanine (111) were chosen; only the first of them was also found in living organisms (4).…”

Improved Preparation of Racemic 2-Amino-3-(heteroaryl)propanoic Acids and Related Compounds Containing a Furan or Thiophene Nucleus

“…7) As a continuation of that work, we have investigated a convenient route to a key intermediate, namely, racemic 3-(furan-2-yl)alanine (1a). This furan derivative (1a) has been synthesized in several ways, e.g., (i) diketopiperazine method, 8) (ii) hydantoin method, 9,10) (iii) rhodanine method, [11][12][13] and (iv) halomethylfuran-acylamidomalonate method. [14][15][16][17][18] However, methods (i-iii) involve reduction using sodium amalgam, and subsequent disposal is damaging to the environment.…”