Acetic Acid → HCID 141573153, compound

Participants

Reaction Steps

The product from c) (210 mg) in DMF (1 ml) was added, at 0° C., to a suspension of 7-[2-(2-aminothiazol-4-yl)-2-((Z)-1-carboxy-1-methylethoxyimino)acetamido]-3-aminomethylceph-3-em-4-carboxylic acid (484 mg) in methanol/water (9:1 ratio; 7 ml) under an argon atmosphere. Sodium cyanoborohydride (63 mg) was added, reaction mixture was stirred for 3 hours at ambient temperature and solvent evaporated under reduced pressure to give a residue. This was dissolved in 10% aqueous acetonitrile (30 ml) containing acetic acid and sodium acetate and purified by preparative HPLC chromatography (Dynamax) using acetonitrile/water containing 0.1% trifluoroacetic acid as eluant to a carboxy-1-methylethoxyimino)acetamido]-3-(4,5-dihydroxy-2-(methoxycarbonylmethyl)benzylaminomethyl)ceph-3-em-4-carboxylic acid (50 mg); NMR (DMSO-d6 /CF3COOH) 1.50(s,3H); 1.53(s,3H); 3.63(s,3H); 3.7(m,2H); 3.92(m,2H); 4.1(m,2H); 5.22(d,1H); 5.9(dd,1H); 6.72(s,1H); 6.95(s,1H); 7.1(s,1H); 8.3(s,1H); 9.1(s,1H); 9.62(d,2H): FAB M/S (M-H)- 678.

Provenance & Evidence