1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 10-Oxo-dec-7-ene-1-sulfonic acid hexylamide

Temperature

0 °C

Under a nitrogen atmosphere, (E)-10-hexylsulfamoyl-dec-3-enoic acid (100 mg, 0.30 mmol) obtained in Step C-3 and (S)-4-isopropyl-5,5-diphenyl-oxazolidine-2-thione (89.2 mg, 0.30 mmol) were dissolved in dichloromethane (3.5 mL), and the mixture was cooled to 0° C. While maintaining the temperature at 0° C., N,N-dimethyl-4-aminopyridine (3.7 mg, 0.03 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (74.7 mg, 0.39 mmol) were added in order, and the mixture was stirred at 0° C. for 2 minutes and at room temperature for 13 hours. To the reaction solution was added an aqueous solution (4.2 mL) of 10% sodium dihydrogen phosphate and ethyl acetate and the mixture was extracted. The organic layer was washed with water and a saturated brine in order, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off. The resulting residue was then purified with SP1 (SiO2 cartridge, 20% ethyl acetate/n-hexane, Rf=0.25) to obtain the target compound, (E)-104(S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-10-oxo-dec-7-ene-1-sulfonic acid hexylamide (ESI (LC/MS positive mode) m/z 613 (M+H); Rt 2.60 min.; 65% purity, 96.8 mg, 53% yield).

1. temperatureWhile maintaining the temperature at 0° C.
2. extractionthe mixture was extracted
3. washThe organic layer was washed with water
4. dry with materiala saturated brine in order, dried over anhydrous sodium sulfate
5. filtrationfiltered
6. distillationThe solvent was distilled off
7. customThe resulting residue was then purified with SP1 (SiO2 cartridge, 20% ethyl acetate/n-hexane, Rf=0.25)

ORD record

ord-bf6995f69dd345afa9420280028f52bb

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266853B2