Triethyl phosphite → 432038-96-5

Participants

Reaction Steps

A solution of 0.28 g of dimedone, 0.13 g of sodium bicarbonate, and 0.06 ml of triethyl phosphite in 1 ml of water and 3 ml of tetrahydrofuran was stirred at room temperature for 10 min. The atmosphere was then replaced by argon, 22.4 mg of palladium acetate was added thereto, and the mixture was stirred for 10 min. 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 (0.66 g) was added thereto, and the mixture was stirred at 40° C. for 2 hr. The reaction mixture was stirred in an ice-water bath for 30 min, and the resultant precipitate was collected by filtration to give 0.47 g of a crude product 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 crude product was dissolved in 2 ml of water, and the solution was filtered through a filter with a pore diameter of 0.45 μm, followed by washing three times with 0.5 ml of water. The filtrate and the wash liquids were combined, and stirring was carried out at 4° C. for 12 hr. The resultant precipitate was collected by filtration to give 0.35 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.

Provenance & Evidence