Water → Ethyl (3-chloro-4-{1,3-dioxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate

HRID 913167노트

반응식

HRID 913167 반응식
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:20](=[O:21])[C:19]3[C:18]([OH:22])=[C:17]4[CH:23]=[CH:24][CH:25]=[CH:26][C:16]4=[C:15]([OH:27])[C:14]=3[C:13]2=[O:28])=[C:8]([Cl:29])[CH:7]=1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].FC(F)(F)S(O[CH2:43][C:44]([F:47])([F:46])[F:45])(=O)=O.O>CN(C=O)C>[Cl:29][C:8]1[CH:7]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:30])[CH:11]=[CH:10][C:9]=1[N:12]1[C:20](=[O:21])[C:19]2[C:18]([O:22][CH2:43][C:44]([F:47])([F:46])[F:45])=[C:17]3[CH:23]=[CH:24][CH:25]=[CH:26][C:16]3=[C:15]([O:27][CH2:43][C:44]([F:45])([F:46])[F:47])[C:14]=2[C:13]1=[O:28]

참가 물질

6

반응물 4

HCID 962WaterHCID 10340Sodium Carbonate2회HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate2회HCID 178470686ethyl 2-[3-chloro-4-(4,9-dihydroxy-1,3-dioxobenzo[f]isoindol-2-yl)phenyl]acetate

생성물 1

HCID 58012483Ethyl (3-chloro-4-{1,3-dioxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate수율 90.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of ethyl[3-chloro-4-(4,9-dihydroxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate (0.30 g, 0.71 mmol) in DMF (3 ml), was added sodium carbonate (0.299 g, 2.82 mmol) followed by 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.490 g, 2.12 mmol). This was stirred at room temperature for 21 hours. Further sodium carbonate (0.11 g, 1.06 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.246 g, 1.06 mmol) was added to the reaction to drive it to completion. This was then heated to 50° C. for 2.5 hours. Water was added to the reaction mixture with rapid stirring. The resulting tan coloured solid was collected by filtration, washed with water and dried in the vacuum oven to give the title compound (0.377 g, 0.64 mmol). LC/MS: Rt=3.98, [MH]+ 590.

후처리

  1. temperatureThis was then heated to 50° C. for 2.5 hours
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried in the vacuum oven

출처 및 근거

ORD 기록
ord-bef9edd4345c44d399da6dba544886a3
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026270B2

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