Chlorosuccinimide → HCID 86591859, compound

Temperature

-78 °C

To a solution of cyclopropylsulfonylamine tert-butyl carbamate (1.0 g, 4.52 mmol) dissolved in THF (10 mL) cooled to −78° C., was added n-BuLi (6.4 mL, 10.2 mmol, 1.6 M in hexane) and the reaction mixture was stirred for 1 h. To this solution was added a THF (10 mL) solution of NCS (0.86 g, 6.34 mmol). After stirred for 5 min, the bath was changed to ice bath and the mixture was stirred for 3 hrs at the temperature. The reaction mixture was diluted with ice water, the pH was adjusted to <4. The aqueous mixtire was extracted with EtOAc. The combined extracts were dried (MgSO4), concentrated and purified by flash chromatography over SiO2 using 0% to 60% EtOAc in hexanes as the eluent to afford 0.98 g (67%) of 1-chloro-cyclopropanesulfonamide-tert-butylcarbamate as a white solid: 1H NMR (500 MHz, CDCl3) δ ppm 1.51 (m, 11H), 2.01 (m, 2H), 7.60 (s, 1H).

1. stirringAfter stirred for 5 min
2. customthe bath was changed to ice bath
3. stirringthe mixture was stirred for 3 hrs at the temperature
4. extractionThe aqueous mixtire was extracted with EtOAc
5. dry with materialThe combined extracts were dried (MgSO4)
6. concentrationconcentrated
7. custompurified by flash chromatography over SiO2 using 0% to 60% EtOAc in hexanes as the eluent

ORD record

ord-9e9f40be993349f9a2f3c4d23913cfe5

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07135462B2