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Potassium Carbonate → (R,Z)-3-(2-{4-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-(prop-1-en-1-yl)phenyl]-3-methylpiperazin-1-yl}-2-oxoethyl)-5-[4-(1-methylethoxy)phenyl]-5-methylimidazolidine-2,4-dione

HRID 1038556
ノート
印刷プレビュー

反応式

HRID 1038556 の反応式
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2([CH3:18])[NH:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])=[CH:7][CH:6]=1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([O:50]COC)([C:46]([F:49])([F:48])[F:47])[C:42]([F:45])([F:44])[F:43])=[CH:37][C:36]=2/[CH:54]=[CH:55]\[CH3:56])[C@H:31]([CH3:57])[CH2:30]1)=[O:28].Cl.C(OCC)(=O)C>CN(C)C=O.C(OCC)(=O)C.O>[F:48][C:46]([F:47])([F:49])[C:41]([C:38]1[CH:39]=[CH:40][C:35]([N:32]2[CH2:33][CH2:34][N:29]([C:27](=[O:28])[CH2:26][N:13]3[C:12](=[O:17])[C@:11]([C:8]4[CH:7]=[CH:6][C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[CH:10][CH:9]=4)([CH3:18])[NH:15][C:14]3=[O:16])[CH2:30][CH:31]2[CH3:57])=[C:36](/[CH:54]=[CH:55]\[CH3:56])[CH:37]=1)([OH:50])[C:42]([F:45])([F:44])[F:43]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 3052153Hydantoin, 5-(p-isopropoxyphenyl)-5-methyl-HCID 21866389Hydrogen chloride-ethyl acetateHCID 86647202HCID 86647202、化合物

生成物 1

HCID 86647201(R,Z)-3-(2-{4-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-(prop-1-en-1-yl)phenyl]-3-methylpiperazin-1-yl}-2-oxoethyl)-5-[4-(1-methylethoxy)phenyl]-5-methylimidazolidine-2,4-dione
収率 83.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

5-[4-(1-Methylethoxy)phenyl]-5-methylimidazolidine-2,4-dione (7.7 mg, 0.0311 mmol) was dissolved in N,N-dimethylformamide (500 μL), added potassium carbonate (8.6 mg, 0.0622 mmol) under ice-cold conditions, and the mixture was stirred at room temperature for 5 minutes. Then, under ice-cold conditions, (R,Z)-2-bromo-1-(4-{4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-(prop-1-en-1-yl)phenyl}-3-methylpiperazin-1-yl)ethanone (17 mg, 0.0311 mmol) was added, and stirred at room temperature for 18 hours. Under ice-cold conditions, the reaction solution was added water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained crude product was dissolved in ethyl acetate (1.0 mL), added a solution of 4N-hydrochloric acid-ethyl acetate (1.0 mg), and stirred at room temperature for 1 hour. Under ice-cold conditions, the reaction solution was added water and a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and (R,Z)-3-(2-{4-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-(prop-1-en-1-yl)phenyl]-3-methylpiperazin-1-yl}-2-oxoethyl)-5-[4-(1-methylethoxy)phenyl]-5-methylimidazolidine-2,4-dione (17.4 mg (yield 83%)) was obtained as a yellow oil.

後処理

  1. stirringstirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained crude product
  7. stirringstirred at room temperature for 1 hour
  8. extractiona saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-b796d39c66c3454a9720b1ab1a7c6506
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08551985B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート