Abstract:The title compound, methyl N-[1-(benzoylamino)-2-methoxy-2-oxoethyl]tryptophanate 2, was synthesized in high yield, via N-alkylation reaction of methyl 2-azido-2-benzamidoacetate with methyl 2-amino-3-(1H-indol-3-yl)propanoate in acetone, with the presence of diisopropylethylamine as a base. The structure of the prepared compound was characterized by 1 H, 13 C NMR in addition to MS, X-Ray diffraction data, and elemental analysis. This compound was tested in vitro for its antibacterial activity against Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus, and Gram-negative bacteria, Escherichia coli, Pseudomonas aeruginosa, and Salmonella enteric. The MIC values showed that the synthesized compound had a bactericidal effect against the strains tested.

The present work covers the recent synthetic of methyl (2R)-2-benzamido-2-{[(1R)-2-methoxy-2-oxo-1-phenylethyl]amino}acetate, via N-alkylation of methyl a-azido glycinate N-benzoylated with methyl 2-amino-2-phenylacetate in methylene chloride and in presence of triethylamine as basic catalyst. The structure of the prepared compound was determined by spectroscopic methods: 1H-NMR, 13C-NMR, MS data, elemental analysis and confirmed by X-Ray diffraction. This compound was screened in vitro for its antibacterial activity against Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa and Salmonella enteric). The MIC values confirmed that the title compound had a bactericidal effect against the strains tested.

In the title compound, C 19 H 20 N 2 O 5 , the dihedral angle between the phenyl rings is 58. 85 (8) , while that between the planes of the methyl acetate groups is 88. 30 (8) . The molecular conformation is also influenced by the presence of an intramolecular N-HÁ Á ÁO hydrogen bond. In the crystal, N-HÁ Á ÁO hydrogen bonds link the molecules, forming chains propagating along the a-axis direction. Structure descriptionThe synthesis of new -AAs (-aminoacetates) and their esters is of international interest because of their extensive applications in enzymology, medicine, pharmacology and industry (Leite et al., 2006;Mikołajczyk, 2005;Joly et al., 2004). Our strategy used nucleophilic substitution of the N-protected methyl -azido glycinate with 2-amino-2-phenylacetate in methylene chloride, in the presence of triethylamine as a base (Boukallaba et al., 2006) to produce the title compound in good yield.In the title molecule (Fig. 1), the dihedral angles between the phenyl rings and those between the planes of the methyl acetate groups are 58.85 (8) and 88.30 (8) respectively. The twisted conformation of the molecule is also influenced by the presence of an intramolecular N-HÁ Á ÁO hydrogen bond (Table 1). In the crystal, N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds (Table 1, Fig. 2) link the molecules into chains propagating along the a-axis direction.

A new compound tetramethyl 1,1′-(2-[{4,5-bis(methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate) (3) was prepared in two steps starting from 2-((4-methylphenyl)sulfonamido)-2-((tosyloxy)methyl)propane-1,3-diylbis(4-methylbenzenesulfonate) (1), with an overall yield of 74%. The key step being the copper-free Huisgen cycloaddition between N-(1,3-diazido-2-(azidomethyl)propan-2-yl)-4-methylbenzenesulfonamide (2) and commercially available dimethyl acetylenedicarboxylate. The chemical structure of compound 3 was determined by IR, 1D and 2D NMR experiments, and elemental analysis.

The title molecule, C 22 H 23 N 3 O 2 , is U-shaped, with a dihedral angle of 80.76 (9) between the indole ring system and the phenyl ring. In the crystal, N-HÁ Á ÁO hydrogen bonds combine with N-HÁ Á Á and C-HÁ Á Á interactions to generate a three-dimensional structure. Structure descriptionThe molecule of the title compound is approximately U-shaped, Fig. 1, with the indole ring system and the benzene ring linked by a complex alaninate chain and with a dihedral angle of 80.76 (9) between them. This conformation is supported by an intramolecular C5-H5Á Á ÁCg3 interaction (Table 1).In the crystal, classical N3-H3NÁ Á ÁO1 hydrogen bonds together with unusual intermolecular N2-H2NÁ Á ÁCg2 contacts and C20-H20Á Á ÁCg1 interactions combine to generate a three dimensional network, Fig. 2. Synthesis and crystallizationTo a solution of 2.6 mmol of N-protected methyl -azidoglycinate and 3.12 mmol of diisopropylethylamine (DIEA) in 10 ml of acetone, 2.86 mmol of 2-amino-3-(1H-indol-3-yl)propanoate was added. The reaction mixture was stirred at room temperature. The solvent was evaporated under reduced pressure. The residue was quenched with saturated aqueous solution of ammonium chloride (20 ml) and extracted with methylene chloride (3 Â 20 ml). The organic layer was dried over sodium sulfate (Na 2 SO 4 ) and the