Acetic Acid → HCID 10646750, 화합물

HRID 1489438노트

반응식

HRID 1489438 반응식
[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]=[CH:14][NH:13][C:12]2=[O:16])=[CH:7][CH:6]=1.[H-].[Na+].[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30](=[O:41])[C@@H:31](OS(C(F)(F)F)(=O)=O)[CH3:32].C(O)(=O)C>CN1CCCC1=O.O1CCCC1.C(OCC)(=O)C.C(OC(C)C)(C)C>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30](=[O:41])[C@H:31]([N:13]1[CH:14]=[CH:15][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)[C:12]1=[O:16])[CH3:32]

참가 물질

9

반응물 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 10493689HCID 10493689, 화합물HCID 10804132HCID 10804132, 화합물

생성물 1

HCID 10646750HCID 10646750, 화합물수율 37.2%

시약·촉매·용매 4

HCID 7914Diisopropyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

1-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (4.6 g) was dissolved in 30 ml of 1-methyl-2-pyrrolidone, to which 0.6 g of 60% sodium hydride in oil was added. The mixture was stirred at room temperature for 0.5 hours. The reaction solution was ice-cooled and added dropwise under nitrogen atmosphere over the period of 5 minutes to a solution of 5.3 g of (2S)-2'-fluoro-2-trifluoromethanesulfonyloxypropiophenone in 50 ml of tetrahydrofuran which was cooled to -40° C. Then, the reaction solution was stirred at -40° to -35° C. for 20 minutes. To the reaction solution was added 2 ml of acetic acid. The mixture was diluted with a mixture of 300 ml of ethyl acetate and 150 ml of diisopropyl ether, washed with 80 ml of water, 0.5N-hydrochloric acid (80 ml×2) and 40 ml of an aqueous solution of sodium chloride successively, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 200 g, eluent; hexane:ethyl acetate:acetic acid=2:1:0.03) and crystallized from diisopropyl ether to give 2.6 g of 1-[(1R)-2-(2-fluorophenyl)-2-oxo-1-methylethyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone as colorless powdery crystals.

후처리

  1. additionwas added
  2. temperaturecooled
  3. temperaturewas cooled to -40° C
  4. stirringThen, the reaction solution was stirred at -40° to -35° C. for 20 minutes
  5. washwashed with 80 ml of water, 0.5N-hydrochloric acid (80 ml×2) and 40 ml of an aqueous solution of sodium chloride successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (silica gel: 200 g, eluent; hexane:ethyl acetate:acetic acid=2:1:0.03)
  9. customcrystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-8692f1a5078b429e9011a2e39e4f95ba
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05677464

반응 노트

불러오는 중…