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

HRID 2067714Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CN=CC=1.[O:21]=[S:22](=[O:24])=[O:23]>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[O:11][C:12]([S:22]([OH:24])(=[O:23])=[O:21])=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-4035de0dd4124628b8b5ab462f12af87
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293895B2

Reaction notes

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