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Triethylamine → HCID 59482647、化合物

HRID 2172341
ノート
印刷プレビュー

反応式

HRID 2172341 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

HCID 59482647HCID 59482647、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b7baadef5ee8485cb8cd9b52d5fc84cc
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09051403B2

反応ノート

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