Acetic Acid → HCID 10766040、化合物

HRID 1489418ノート

反応式

HRID 1489418 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]=[CH:14][NH:13][C:12]2=[O:16])=[CH:7][CH:6]=1.FC(F)(F)S(O[C@@H:27]([CH3:38])[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])(=O)=O.C(O)(=O)C>CN1CCCC1=O.[H-].[Na+].O1CCCC1.C(OCC)(=O)C>[F:20][C:2]([F:1])([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][N:13]([C@H:27]([CH3:38])[C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])[C:12]2=[O:16])=[CH:7][CH:6]=1

参加物

8

反応物 3

HCID 176Acetic AcidHCID 10493689HCID 10493689、化合物HCID 10881508Phenylmethyl (2S)-2-[[(trifluoromethyl)sulfonyl]oxy]propanoate

生成物 1

HCID 10766040HCID 10766040、化合物収率 85%

試薬・触媒・溶媒 4

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

1-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (4 g) was dissolved in 30 ml of 1-methyl-2-pyrrolidone, to which 60% sodium hydride in oil (0.55 g) was added. The mixture was vigorously stirred at room temperature for 30 minutes and then added to a solution of 5.2 g of benzyl (2S)-2-trifluoromethanesulfonyloxypropionate (prepared in Example 3) in 80 ml of tetrahydrofuran under nitrogen atmosphere at -40° to -50° C. over the period of 10 minutes. The mixture was stirred at -20° to -40° C. for 50 minutes, followed by addition of 9.6 ml of acetic acid. Then, the reaction solution was diluted with 100 ml of ethyl acetate, washed with 50 ml of water, 1N-hydrochloric acid (50 ml×2) and 50 ml of an aqueous solution of sodium chloride successively, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (silica gel: 200 g, eluent; hexane:ethyl acetate=2:3) to give 5.3 g of benzyl (2R)-2-[3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2,3-dihydro-2-oxo-1H-imidazol-1-yl]propionate (yield: 85%) as colorless powdery crystals.

後処理

  1. additionwas added
  2. stirringThe mixture was stirred at -20° to -40° C. for 50 minutes
  3. washwashed with 50 ml of water, 1N-hydrochloric acid (50 ml×2) and 50 ml of an aqueous solution of sodium chloride successively
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel chromatography (silica gel: 200 g, eluent; hexane:ethyl acetate=2:3)

出典と根拠

ORDレコード
ord-e9edfe51366a444db31289e59b3b9144
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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