Chlorosulfonyl isocyanate → HCID 86741567, compound

Participants

Reaction Conditions

Reaction Steps

(S)-3-[[(Phenylmethoxy)carbonyl]amino]-2azetidinone (2 g) was suspended in 200 ml of dry tetrahydrofuran and cooled to -70° C. Chlorosulfonylisocyanate (1.4 g) dissolved in 7 ml of dry tetrahydrofuran was added with stirring. The temperature was allowed to rise to 0° C. and this temperature was maintained for 10 minutes. Afterwards it was cooled to -40° C., 1.2 g of triethylamine was dropped in and 2.9 g of 1-[2-[(t-butoxycarbonyl)amino]ethyl]-3-carbamoyl-2-oxoimidazolidine was added. This mixture was stirred at room temperature for 14 hours. Following the work-up procedure described in example 34A yielded 5.4 g of (S)-[1-[[[[[[3-[2-(t-butoxycarbonylamino)ethyl]-2-oxo-1-imidazolidinyl]carbonyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3azetidinyl]carbamic acid, phenylmethyl ester, potassium salt.

Provenance & Evidence