HCID 10710636、化合物 → HCID 10813782、化合物

HRID 1489424ノート

反応式

HRID 1489424 の反応式
[F:1][C:2]([F:20])([CH:17]([F:19])[F:18])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[N:14][NH:13][C:12]2=[O:16])=[CH:7][CH:6]=1.[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[C:29](=[O:40])[C@@H:30](OS(C(F)(F)F)(=O)=O)[CH3:31]>CN1CCCC1=O.[H-].[Na+].O1CCCC1.C(O)(=O)C.C(OCC)(=O)C>[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[C:29](=[O:40])[C@H:30]([N:13]1[C:12](=[O:16])[N:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][C:2]([F:1])([F:20])[CH:17]([F:19])[F:18])=[CH:6][CH:7]=2)[CH:15]=[N:14]1)[CH3:31]

参加物

8

反応物 2

HCID 10710636HCID 10710636、化合物HCID 10779907HCID 10779907、化合物

生成物 1

HCID 10813782HCID 10813782、化合物収率 55.5%

試薬・触媒・溶媒 5

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒HCID 24758Sodium hydride溶媒

実験手順

4-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (6.12 g) was dissolved in 60 ml of 1-methyl-2-pyrrolidone, to which 60% of sodium hydride in oil (0.80 g) was added, and the mixture was stirred at room temperature for 3 hours. The reaction solution was ice-cooled and added dropwise under nitrogen atmosphere over the period of 25 minutes to a solution of 7.32 g of (2S)-2',4'-difluoro-2-trifluoromethanesulfonyloxypropiophenone in 180 ml of tetrahydrofuran which was cooled to -50° C. Then, the reaction temperature was raised to -30° C. over the period of 10 minutes. After stirring for 30 minutes, the reaction solution was diluted with 10 ml of acetic acid and 500 ml of ethyl acetate, washed with water (300 ml×2), 0.5N-hydrochloric acid (400 ml×2) and 300 ml of a saturated aqueous solution of sodium chloride successively, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 250 g, eluent; hexane:ethyl acetate:acetic acid=3:1:0.04), and dissolved in 12 ml of diisopropyl ether. The solution was allowed to stand for 1 hour with ice cooling. The deposited insoluble substance was removed by filtration and the solution was concentrated under reduced pressure to give 5.36 g of 2-[(1R)-2-(2,4-difluorophenyl)-2-oxo-1-methylethyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone as a pale yellow viscous substance.

後処理

  1. additionwas added
  2. temperaturecooled
  3. temperaturewas cooled to -50° C
  4. temperatureThen, the reaction temperature was raised to -30° C. over the period of 10 minutes
  5. stirringAfter stirring for 30 minutes
  6. washwashed with water (300 ml×2), 0.5N-hydrochloric acid (400 ml×2) and 300 ml of a saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel chromatography (silica gel: 250 g, eluent; hexane:ethyl acetate:acetic acid=3:1:0.04)
  10. dissolutiondissolved in 12 ml of diisopropyl ether
  11. waitto stand for 1 hour with ice cooling
  12. customThe deposited insoluble substance was removed by filtration
  13. concentrationthe solution was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-2c485e55687a4008b7c95957093cf600
出典データセット
uspto-grants-1997_10
特許番号
US05677464

反応ノート

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