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Triethylamine → HCID 59482647, 화합물

HRID 2172341
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HRID 2172341 반응식
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:13])[C:10]([CH3:12])=[CH2:11])=[CH:4][CH:3]=1.[F:16][C:17]([F:32])([S:28](F)(=[O:30])=[O:29])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[S:20](F)(=[O:22])=[O:21].C(N(CC)CC)C.[F:40][C:41]([F:47])([F:46])[S:42]([NH2:45])(=[O:44])=[O:43]>C1COCC1.C(OCC)(=O)C>[F:40][C:41]([F:47])([F:46])[S:42]([NH:45][S:20]([C:19]([F:25])([F:24])[C:18]([F:27])([F:26])[C:17]([F:32])([F:16])[S:28]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:13])[C:10]([CH3:12])=[CH2:11])=[CH:14][CH:15]=1)(=[O:30])=[O:29])(=[O:22])=[O:21])(=[O:44])=[O:43]
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 79001TrifluoromethylsulfonamideHCID 216154N-MethacryloyltyramineHCID 11130879Perfluoropropane-1,3-disulfonyl fluoride

생성물 1

HCID 59482647HCID 59482647, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b7baadef5ee8485cb8cd9b52d5fc84cc
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09051403B2

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