Water → HCID 19748802, compound

Participants

Reaction Conditions

Reaction Steps

The material prepared above in Example 24, Method B, Step A (3.3 kg) was cooled to 5° C. under a N2 blanket and chlorosulfonyl isocyanate (2.1 L) was added with stirring over 1 hr. The mixture was then stirred at 8° C. for 45 hr and then cooled to 0° C., diluted with toluene (5 L), and then added to a mixture of H2O (60 L), ice (20 L), NaHCO3 (13 kg) and Na2SO3 (7.5 kg). This mixture was stirred at 20° C. for 13 hr before being filtered through Celite. The pad was washed with EtOAc (7 L) and the two layers of the filtrate were separated. The aqueous layer was further extracted with EtOAc (12 L) and the combined organic layers were washed with brine (8 L) before being concentrated in vacuo. Toluene (2 L) was then added to the residue and the solution was re-concentrated to dryness to give 4.57 kg of a light yellow oil which was of sufficient purity for use in the next step.

Provenance & Evidence