Chloroform → HCID 131713388, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[3-(2,4,5-trimethyl-1H-imidazol-1-yl)propyl]-1-piperidine (0.75 g, 0.0032 M) and dimethylformamide dimethylacetal (20 ml) was heated at 100° C. for 9 hrs. The reaction was stripped to dryness to yield 4-[3-(2,4,5-trimethyl-1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde dimethylacetal. The solution of the above piperidine carboxaldehyde dimethylacetal in chloroform (4 ml) was then added to a mixture of 6-aminopenicillanic acid (0.67 g, 0.003 M) and diisopropylethylamine (0.47 ml) in chloroform (12 ml) at 0° C. The reaction was stirred at 0° C. for 1 hr and room temperature for 3 hrs. Solvent was removed and water (15 ml) was added. After being washed with diethyl ether, the aqueous solution, acidified to a pH 3 to about 3.5, was purified on Sephadex LH 20 columns to give [2S-(2alpha,5alpha,6beta)]-6[ [4-[3-[2,4,5-trimethyl-1H-imidazol-1-yl)propyl]-1-piperidinyl]methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid hydrate hydrochloride (0.71 g, 46% yield).

Provenance & Evidence