N-Methylaniline → 432038-96-5

Participants

Reaction Steps

Sodium bicarbonate (6.72 g), 10.4 ml of N-methylaniline, and 4.8 ml of triethyl phosphite were added in that order to 320 ml of a mixed liquid of 2-propanol:water=3:2. The atmosphere was replaced by argon, and the mixture was stirred at room temperature for 15 min. Palladium acetate (0.90 g) was then added thereto, and the mixture was stirred for 10 min. A solution of 59.31 g of allyl (1S,5R,6S)-2-[7-(1-carbamoylmethylpyridinium-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate iodide in 400 ml of a mixed liquid of 2-propanol:water=3:2 was added to the reaction mixture, and the mixture was stirred at 30° C. for one hr. 2-Propanol (80 ml) was added to the reaction mixture, and the mixture was stirred in an ice-water bath for one hr. The resultant precipitate was then collected by filtration and was washed with 265 ml of a cooled mixed liquid of 2-propanol:water=2:1, 53 ml of 2-propanol, and 106 ml of acetone in that order to give 7.168 g of (1S,5R,6S)-2-[7-(1-carbamoylmethylpyridinium-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate. This product was analyzed by NMR. The results were in agreement with the results of analysis in Example A-2.

Provenance & Evidence