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 913167ノート

反応式

HRID 913167 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium Carbonate2 回HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate2 回HCID 178470686ethyl 2-[3-chloro-4-(4,9-dihydroxy-1,3-dioxobenzo[f]isoindol-2-yl)phenyl]acetate

生成物 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)acetate収率 90.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bef9edd4345c44d399da6dba544886a3
出典データセット
uspto-grants-2011_09
特許番号
US08026270B2

反応ノート

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