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Sodium Hydroxide → Sodium 3-(4-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

HRID 423377
ノート
印刷プレビュー

反応式

HRID 423377 の反応式
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:17]=3[CH:18]=[CH:19][N:20]4[CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])[N:12]=2)=[CH:7][C:6]=1[C:32]([F:35])([F:34])[F:33])[CH3:3].[OH-].[Na+:37]>C(O)C>[CH3:3][CH:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:17]=3[CH:18]=[CH:19][N:20]4[CH2:25][CH2:26][C:27]([O-:29])=[O:28])[N:12]=2)=[CH:7][C:6]=1[C:32]([F:35])([F:34])[F:33])[CH3:1].[Na+:37]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 59318349Ethyl 3-(4-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

生成物 1

HCID 66677381Sodium 3-(4-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate収率 69.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

To a suspension of ethyl 3-(4-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate (D72) (81 mg, 0.17 mmol) in ethanol (8 mL) was added aqueous sodium hydroxide (2M, 0.8 mL, 1.6 mmol) and the reaction heated to 50° C. to dissolve the reagents before heating at 40° C. for 1 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (20 mL) and water (20 mL) and acidified with aqueous hydrochloric acid (2M). The aqueous phase was extracted with further ethyl acetate (2×20 mL) and the combined organic extracts dried (phase separator) and concentrated in vacuo. The solid was then dissolved in acetonitrile and water with addition of an equimolar amount of sodium hydroxide (2M) before the solution was freeze-dried to give the title compound (57 mg). δH (d6-DMSO, 400 MHz): 8.44 (1H, dd), 8.35 (1H, d), 7.93 (1H, dd), 7.74 (1H, d), 7.65-7.54 (2H, m), 7.31 (1H, app. t), 7.00 (1H, dd) 4.99 (1H, septet), 4.38 (2H, t), 2.34 (2H, t), 1.36 (6H, d). MS (ES): C23H20F3N3O4 requires 459; found 460 (MH+).

後処理

  1. dissolutionto dissolve the reagents
  2. temperaturebefore heating at 40° C. for 1 h
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between ethyl acetate (20 mL) and water (20 mL)
  5. extractionThe aqueous phase was extracted with further ethyl acetate (2×20 mL)
  6. customthe combined organic extracts dried (phase separator)
  7. concentrationconcentrated in vacuo
  8. dissolutionThe solid was then dissolved in acetonitrile
  9. additionwater with addition of an equimolar amount of sodium hydroxide (2M) before the solution
  10. customwas freeze-dried

出典と根拠

ORDレコード
ord-8da687783cdd4684a3b20c9cfd05b9cd
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08101775B2

反応ノート

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