Triethylsilane → Ceftobiprole Medocaril Sodium

Participants

Reaction Conditions

Reaction Steps

A mixture of 40 mg 7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyimino-acetylamino]-3-[1′-(5-methyl-2-oxo-[1,3]dioxol-4-ylmethoxycarbonyl)-2-oxo-[1,3′]bipyrrolidinyl-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester and 20 mg triethylsilane is dissolved in 0.30 ml trifluoroacetic acid. The resulting solution is stirred at 0° C. for 15 min. The solvent is evaporated under aspirator vacuum and the residue is triturated with diethyl ether. The solid is collected by filtration and washed with diethyl ether to yield 23 mg of the title compound as beige powder. MS: M−H=689.3. 1H-NMR (d6-DMSO): 13.8 (s, 1H, COOH); 11.9 (s, 1H, OH); 9.45 (d, J=8.4, 1H, NH); 8.05 (s, 2H, NH2); 7.31(s, 1H, HC═C); 5.86 (dd, J=8.4; 4.8, 1H CH); 5.17 (d, J=8.4, 1H CH); 4.61 (m, 1H CH); 3.85 (m, 2H CH2); 3.55-3.35 (m, 6H 3×CH2); 3.1 (m, 1H); 2.9 (m, 1H); 2.15 (s, 3H, CH3); 2.05 (m, 2H CH2).

Provenance & Evidence