Water → HCID 19748802, compound

Temperature

0 °C

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.

1. customThe material prepared above in Example 24, Method B, Step A (3.3 kg)
2. additionwas added
3. stirringThe mixture was then stirred at 8° C. for 45 hr
4. stirringThis mixture was stirred at 20° C. for 13 hr
5. filtrationbefore being filtered through Celite
6. washThe pad was washed with EtOAc (7 L)
7. customthe two layers of the filtrate were separated
8. extractionThe aqueous layer was further extracted with EtOAc (12 L)
9. washthe combined organic layers were washed with brine (8 L)
10. concentrationbefore being concentrated in vacuo
11. additionToluene (2 L) was then added to the residue
12. concentrationthe solution was re-concentrated to dryness

ORD record

ord-52bcfe4839314f2cb8e9cf048583ea78

Source dataset

uspto-grants-1993_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05229381