Triethylamine → 7-Cyanomethylthioacetamido-3-cephem-3-ol-4-carboxylic acid Benzhydryl Ester

Participants

Reaction Steps

7-Amino-3-cephem-3ol-4-carboxylic acid benzhydryl ester p-toluenesulfonate salt [Helv. Chim. Acta 57, 1919 (1974)], (242 mg.) is dissolved in methylene chloride (5 ml.), cooled in an ice bath, and cyanomethylthioacetyl chloride (68 mg.) in methylene chloride (3 ml.) is added, followed by 125 μl of triethylamine. The mixture is stirred for 3.5 hours at 0°-5° and then is allowed to stand overnight in the refrigerator. After diluting with methylene chloride, the reaction mixture is washed with water, then with pH 4 buffer, and dried (Na2SO4). Solvent is removed in vacuo yielding the desired product as a oil (204 mg.); NMR (CDCl3, δ) 3.33 (m,CH2), 3.45 (s, NCCH2SCH2 --) 5.05 (d, J=4.5 Hz, H6), 5.65 (q. J=4.5, 9Hz, H7), 6.93 (s,CHφ2), 7.33 (s, aromatic H's), 7.80 (d, J=9Hz, NH); νmax (CH2Cl2) 3380, 3310, 2225, 1785, 1735, 1690 cm-1.

Provenance & Evidence