Acetic Acid → HCID 88473887, compound

Participants

Reaction Steps

7-[2-(2-tritylaminothiazol-4-yl)-2((Z)-1-t-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-cyanothiomethylceph-3-em-4-carboxylic acid (10 g) was dissolved in CH3CN (100 ml) and treated, quickly, dropwise at room temperature, with a mixture of 1,3,5-THT (4.2 g, 4.6 ml) and diisopropylamine (3.1 g, 4.1 ml). After 15 min at room temperature the solution was poured into a mixture of toluene (500 ml) and glacial acetic acid (50 ml) and extracted several times with brine. The organic phase was dried over MgSO4, filtered through celite and evaporated to give a foam. Trituration of the foam with ether gave 3-ethylaminomethyl-7-[2-(2-tritylamino-thiazol-4-yl)-2((Z)-1-t-butoxycarbonyl-1-methylethoxy-imino)-acetamido]ceph-3-em-4-carboxylic acid as a granular solid (9.08 g, 92% yield) NMR (200 MHzd6DMSO+CD3COOD): 1.17(t,3H); 1.32(s,9H); 1.39(s,3H); 1.40(s,3H); 2.96 (q,2H); 3.54(d,1H); 3.59(d,1H); 3.65(d,1H); 3.86(d,1H); 5.08(d,1H); 5.69(d,1H); 6.68(s,1H); 7.1-7.4(m,15H).

Provenance & Evidence