Sulfur trioxide-pyridine → 5-(Tert-butoxycarbonylaminomethyl)furan-2-sulfonic acid

온도

0 °C

A solution of 2-(tert-butoxycarbonylaminomethyl)-furan (9.8 g, 50 mmol) in 150 mL of dichloromethane was added into a flask, and the reaction mixture was cooled to 0° C. in an ice bath. A solution of pyridine-sulfur trioxide adduct (15.9 g, 100 mmol) in 100 mL of dichloromethane were added dropwise. Upon completion of the addition, the reaction mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for additional 8 h. After the completion of the reaction, the reaction mixture was then extracted with water (400 mL×2). Aqueous hydrochloric acid (10%) was slowly added dropwise to the aqueous layer. The aqueous layer was adjusted to pH 6.5-7, and extracted with dichloromethane (500 mL×2). The organic layer was washed by saturated brine, and concentrated under reduced pressure to give 5.5 g (40.0% yield) of 5-(tert-butoxycarbonylaminomethyl)furan-2-sulfonic acid.

1. additionUpon completion of the addition
2. temperatureto warm to room temperature
3. customAfter the completion of the reaction
4. extractionthe reaction mixture was then extracted with water (400 mL×2)
5. additionAqueous hydrochloric acid (10%) was slowly added dropwise to the aqueous layer
6. extractionextracted with dichloromethane (500 mL×2)
7. washThe organic layer was washed by saturated brine
8. concentrationconcentrated under reduced pressure

ORD 기록

ord-4035de0dd4124628b8b5ab462f12af87

출처 데이터셋

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08293895B2