Synthesis and Crystal Structure of 3-(Pyrrole-2′-carboxamido)propanoic Acid·(1/2)H_2O

1 INTRODUCTION Pyrrole and its derivatives have attracted much attention due to their chemical properties as well as biological activities1]. They have been widely used to produce pharmaceutical, essences, biochemicals, etc. It has been found that a great number of pyrrole derivatives present antitumor and antiviral activi- ties2 ~ 5]. During our searches for bioactive com- pounds, a series of pyrrole derivatives were synthe- sized6, 7]. We report here the synthesis of 3-(pyrrole- 2?-…

Synthesis and Crystal Structure of 3-(Pyrrole-2′-carboxamido)propanoic Acid·(1/2)H_2O

3-(Pyrrole-2?-carboxamido)propanoic acid I has been synthesized from the reaction of β-alanine methyl ester with 2-trichloroacetylpyrrole followed by saponifying and acidating in 85.4% yield, and the crystal structure of 3-(pyrrole-2?-carboxamido)propanoic acid· (1/2)H2O (C8H11N2O3.5, Mr = 191.19) was obtained and determined by X-ray diffraction method. The crystal is of monoclinic, space group C2/c with a = 19.010(4), b = 8.3515(17), c = 13.788(3) ?, β = 125.88(3)o, V = 1773.6(6) ?3, Z = 8, Dc = 1.432 g/cm3, λ = 0.71073 ?, μ(MoKα) = 0.114 mm?1 and F(000) = 768. The structure was refined to R = 0.0354 and wR = 0.0942 for 1642 observed reflections with I > 2σ(I). It is revealed that the title compound has one pyrrole ring and one propionic acid subchain linked by an amido bond at C(4), and there are 8 molecules of com- pound I and 4 crystal water molecules in each unit cell. The supramolecular layers are stabilized by the hydrogen bonds of N(2) H…O(2), N(1) H…O(4), O(4) H(1W)…O(2) and O(3) H…O(1).