Triethylamine → HCID 86741568, compound

Participants

Reaction Conditions

Reaction Steps

(S)-3-[[(Phenylmethoxy)carbonyl]amino]-2-azetidinone (1.5 g) was suspended in 100 ml of dry tetrahydrofuran and cooled to -70° C. Chlorosulfonylisocyanate (1.1 g) dissolved in 10 ml of dry tetrahydrofuran was dropped in with stirring. The temperature was allowed to rise to 0° C. and maintained there for 20 minutes, followed by cooling to -40° C. Triethylamine (0.9 g) and 2.8 g of 1-carbamoyl-2-oxo-3-[2-[(triphenylmethyl)oxy]ethyl]imidazolidine were added and the mixture was stirred at room temperature for 14 hours. The solvent was removed in vacuo and the work-up procedure of example 34A was followed yielding 4.3 g of (S)-[1-[[[[[[3-(2-hydroxyethyl)-2-oxo-1-imidazolidinyl]carbonyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester, potassium salt.

Provenance & Evidence