Trifluoroacetic acid → HCID 131711162, compound

Participants

Reaction Steps

To a solution of 3-(2-tertiary butoxycarbonylhydrazono)methyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid (247 mg) in methylene chloride (1 ml) are added anisole (0.6 ml) and trifluoroacetic acid (0.6 ml), and the mixture is kept at room temperature for 1 hour. After removing trifluoroacetic acid and methylene chloride, the reaction mixture is diluted with ether. The separated cyrstals are collected by filtration and dried to give 3-hydrazonomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid in nearly quantitative yield. m.p. 164°-169° C (decomposition). IR: νmaxNujol 3260, 1787, 1657, 1542cm-1. UV: λmaxCH3OH 230.5nm(ε=12900); 304nm(ε=6900); 402nm(ε=12400). NMR: δd 6-DMSO (60MHz) 3.79s2H, 3,84d(12Hz)2H, 5.20d(5Hz)1H, 5.84dd(8;5Hz)1H, 6.8-7.5m3H, 7.55s+7.78s1H, 9.12d(8Hz)1H. [α]D23.5 +66.2°(c=0.5022, DMSO).

Provenance & Evidence