Acetaldehyde → HCID 67929082, compound

Participants

Reaction Steps

3-Aminomethyl-7-(t-butoxycarbonylaminoceph-3-em-4-carboxylic acid (987 mg at approximately 71% purity, equivalent to 700 mgs pure material) was added to a rapidly stirred solution of Et3N (215 mg, 0.294 ml) at ambient temperature: it did not dissolve completely. The mixture was stirred for 30 minutes, then NaCNBH3 (132 mg) was added, followed by acetaldehyde (0.119 ml, 93.7 mg) as a solution in methanol, over 40 minutes by infusion pump. The mixture was stirred for 1 hour at ambient temperature after which HPLC showed much starting material still remaining. A further 0.018 ml of acetaldehyde was added in one portion over about 20 seconds. HPLC after a further 30 minutes showed less starting material present. The mixture was evaporated to a foam, then dissolved in 50 ml water adjusted to pH 2-3 with acetic acid, and purified by medium pressure chromatography on HP-20 ss column using gradient elution with water up to 25% v/v acetonitrile. The product eluted at 13-15% acetonitrile.

Provenance & Evidence