Sodium Chloride → HCID 57785632, compound

Temperature

0 °C

A three-neck round bottom flask equipped with a reflux condenser was charged with chlorosulfonyl isocyanate (2.6 ml, 29.9 mol) and cooled to 0° C. Formic acid (1.13 mL, 29.9 mol) was added dropwise with rapid stirring and with rapid gas evolution observed. Upon complete addition of formic acid, the reaction was allowed to warm to room temperature. After 2 h, the reaction vessel was cooled to 0° C. and (1-difluoromethyl-cyclopropoxy)-triisopropyl-silane (500 mg, 1.89 mol) dissolved in NMP (5 mL) was added dropwise via an addition funnel. The mixture was warmed to RT and TBAF (7 ml, 7 mmol) was added. Stir mixture four days. The reaction mixture was poured into cold saturated aqueous NaCl and extracted with EtOAc two times. After removal of the separated organic solvent, the crude product was, purified by column chromatography on silica to provide sulfamic acid 1-difluoromethyl-cyclopropyl ester (10 mg, 2.8% yield): 1H NMR (CDCl3, 300 MHz) δ 6.24 (t, 1H), 5.18 (s, 2H), 1.49 (m, 2H), 1.19 (m, 2H).

1. customA three-neck round bottom flask equipped with a reflux condenser
2. temperatureto warm to room temperature
3. temperaturethe reaction vessel was cooled to 0° C.
4. additionwas added dropwise via an addition funnel
5. temperatureThe mixture was warmed to RT
6. stirringStir mixture four days
7. extractionextracted with EtOAc two times
8. customAfter removal of the separated organic solvent
9. custompurified by column chromatography on silica

ORD record

ord-0a1015e4400a40d9ba5f648b253c4f28

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513186B2