Triethylamine → HCID 59482647, compound

Temperature

50 °C

6.95 Gram of N-(4-hydroxyphenethyl)methacrylamide and 10.7 g of 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonyldifluoride were dissolved in 80 mL of THF, and 80 mL of triethylamine was added thereto. The resulting mixture was stirred at 50° C. for 2 hours, and 5.56 g of trifluoromethanesulfonamide was added thereto. The mixture was further stirred at 80° C. for 4 hours. After adding 200 mL of ethyl acetate, the organic layer was washed, in sequence, twice with dilute hydrochloric acid and twice with water and dried over sodium sulfate. The solvent was concentrated, and the brown oil as residue was dissolved in 200 ml of methanol. Thereto, 10 g of sodium hydrogencarbonate as solid was added, and the mixture was stirred at 50° C. for 4 hours. After adding 200 mL of ethyl acetate, the organic layer was washed, in sequence, twice with saturated brine and twice with water and dried over sodium sulfate to obtain 12.2 g of N-(trifluoromethanesulfonyl)-1,1,2,2,3,3-hexafluoro-3-((4-(2-(methacrylamido)ethyl)phenoxy)sulfonyl)-1-propanesulfonamide solution salt as a brown oil. Thereafter, 12.2 g of this brown oil was dissolved in 100 mL of methanol, and 6.43 g of triphenylsulfonium bromide was added thereto, followed by stirring at room temperature for 3 hours. After adding 200 mL of chloroform, the organic layer was washed with water, and the solvent was concentrated, as a result, 14.0 g of a brown transparent oily compound was obtained. 1H-NMR (300 MHz, CDCl3) δ 1.91 (s, 3H), 2.87 (t, 2H), 3.50 (quartet, 2H), 5.28 (s, 1H), 5.66 (s, 1H), 6.05 (bs, 1H), 7.20 (d, 2H), 7.27 (d, 2H), 7.63-7.77 (m, 15H), 19F-NMR (300 MHz, CDCl3) δ −78.65 (s, 3F), −107.8 (m, 2F), −112.4 (t, 2F), −118.0 (m, 2F).

1. stirringThe mixture was further stirred at 80° C. for 4 hours
2. washthe organic layer was washed, in sequence, twice with dilute hydrochloric acid and twice with water
3. dry with materialdried over sodium sulfate
4. concentrationThe solvent was concentrated
5. dissolutionthe brown oil as residue was dissolved in 200 ml of methanol
6. additionThereto, 10 g of sodium hydrogencarbonate as solid was added
7. stirringthe mixture was stirred at 50° C. for 4 hours
8. additionAfter adding 200 mL of ethyl acetate
9. washthe organic layer was washed, in sequence, twice with saturated brine and twice with water
10. dry with materialdried over sodium sulfate

ORD record

ord-b7baadef5ee8485cb8cd9b52d5fc84cc

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051403B2