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 2214387노트

반응식

HRID 2214387 반응식
[CH3:1][O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[C:17]([NH:19][C:20](=[O:29])[CH2:21][C:22](O)(O)[C:23]([F:26])([F:25])[F:24])[C:16]([F:30])=[CH:15][C:14]=1[Cl:31].O1CCCC1.C(O)(=O)C.[O-:42][C:43]#[N:44].[K+]>O>[Cl:31][C:14]1[CH:15]=[C:16]([F:30])[C:17]([N:19]2[C:20](=[O:29])[CH:21]=[C:22]([C:23]([F:26])([F:25])[F:24])[NH:44][C:43]2=[O:42])=[CH:18][C:13]=1[O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]([O:2][CH3:1])=[O:32]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ea1d3dc69814a1597c3ed55fab14d00
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109148B2

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