Acetic Acid → Methyl [2-{2-chloro-4-fluoro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenoxy]acetate

HRID 493944ノート

反応式

HRID 493944 の反応式
O[C:2](O)([C:28]([F:31])([F:30])[F:29])[CH2:3][C:4]([NH:6][C:7]1[C:8]([F:27])=[CH:9][C:10]([Cl:26])=[C:11]([CH:25]=1)[O:12][C:13]1[CH:24]=[CH:23][CH:22]=[CH:21][C:14]=1[O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:5].O1CCCC1.C(O)(=O)C.[O-:42][C:43]#[N:44].[K+]>O>[Cl:26][C:10]1[CH:9]=[C:8]([F:27])[C:7]([N:6]2[C:4](=[O:5])[CH:3]=[C:2]([C:28]([F:31])([F:30])[F:29])[NH:44][C:43]2=[O:42])=[CH:25][C:11]=1[O:12][C:13]1[CH:24]=[CH:23][CH:22]=[CH:21][C:14]=1[O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 11378442Potassium cyanateHCID 21947104Methyl[2-(5-{3,3-dihydroxy-4,4,4-trifluorobutyryl}amino-2-chloro-4-fluorophenoxy)phenoxy]acetate

生成物 1

HCID 12115501Methyl [2-{2-chloro-4-fluoro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenoxy]acetate収率 66%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 1.0 g of crude methyl [2 -(5-{3,3-dihydroxy-4,4,4-trifluorobutyryl}amino-2-chloro-4-fluorophenoxy)phenoxy]acetate and 3 ml of tetrahydrofuran were added 4 ml of acetic acid and 0.87 g of potassium cyanate, and the mixture was stirred at room temperature for 6 hours and then heated at reflux at 120° C. for 2 hours. After cooling, 30 ml of water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.67 g of methyl [2-{2-chloro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-4-fluorophenoxy}phenoxy]acetate.

後処理

  1. temperatureheated
  2. temperatureat reflux at 120° C. for 2 hours
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-665f7a6406c84767be6b125220ca4365
出典データセット
uspto-grants-2009_05
特許番号
US07538072B2

反応ノート

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