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Hydrochloric Acid → 3-(2-(4-fluoro-1H-indol-2-yl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)pyridin-3-yl)propanoic acid

HRID 595745
ノート
印刷プレビュー

反応式

HRID 595745 の反応式
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]1[C:16]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:15][CH:14]=[C:13]([C:24]3[C:25]([N:44]([CH3:49])[S:45]([CH3:48])(=[O:47])=[O:46])=[CH:26][C:27]4[O:31][C:30]([C:32]5[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=5)=[C:29]([C:39](=[O:42])[NH:40][CH3:41])[C:28]=4[CH:43]=3)[N:12]=1)[NH:6]2.O.[OH-].[Li+].CO.Cl>C1COCC1.CCOC(C)=O.O>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]1[C:16]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:15][CH:14]=[C:13]([C:24]3[C:25]([N:44]([CH3:49])[S:45]([CH3:48])(=[O:46])=[O:47])=[CH:26][C:27]4[O:31][C:30]([C:32]5[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=5)=[C:29]([C:39](=[O:42])[NH:40][CH3:41])[C:28]=4[CH:43]=3)[N:12]=1)[NH:6]2
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 90333603ethyl 3-(2-(4-fluoro-1H-indol-2-yl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)pyridin-3-yl)propanoate

生成物 1

HCID 903334323-(2-(4-fluoro-1H-indol-2-yl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)pyridin-3-yl)propanoic acid

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of ethyl 3-(2-(4-fluoro-1H-indol-2-yl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)pyridin-3-yl)propanoate (91 mg, 0.133 mmol) and lithium hydroxide monohydrate (27.8 mg, 0.663 mmol) were suspended in THF (0.53 mL), MeOH (0.27 mL), and H2O (0.2 mL). The resultant mixture was stirred at ambient temperature overnight then cooled in an ice bath and acidified to pH 2 with 1 N HCl. The mixture was then diluted with EtOAc and H2O, separated into layers and the aqueous layer extracted with EtOAc (2×). The combined organic layers were washed with brine (4×) until last brine wash was pH 7 then were dried over MgSO4, filtered, and concentrated in vacuo. The resulting product was azeotroped from CH3CN (4×) and used as a tan solid without further purification. MS (M+H)+: 659.

後処理

  1. temperaturethen cooled in an ice bath
  2. customseparated into layers
  3. extractionthe aqueous layer extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine (4×) until last brine
  5. washwash
  6. dry with materialthen were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting product was azeotroped from CH3CN (4×)
  10. customused as a tan solid without further purification

出典と根拠

ORDレコード
ord-fe9730e97aa742f9ab63defaab1951ea
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09243002B2

反応ノート

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