Methanol → 3-(6-Chloro-1-isothiazol-4-yl-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid

HRID 1466824ノート

反応式

HRID 1466824 の反応式
C([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11][C:12]2[C:20]3[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=3)[N:14]([C:22]3[CH:23]=[N:24][S:25][CH:26]=3)[C:13]=2[CH3:27])[CH:6]=1)C.CO.O[Li].O>C1COCC1.O.CCOC(C)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:21][C:17]1[CH:16]=[C:15]2[C:20]([C:12]([S:11][C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[C:4]([OH:28])=[O:3])=[C:13]([CH3:27])[N:14]2[C:22]2[CH:23]=[N:24][S:25][CH:26]=2)=[CH:19][CH:18]=1

参加物

8

反応物 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 667657083-(6-Chloro-1-isothiazol-4-yl-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid ethyl ester

生成物 1

HCID 568382563-(6-Chloro-1-isothiazol-4-yl-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid

試薬・触媒・溶媒 4

HCID 311Citric Acid溶媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-(6-Chloro-1-isothiazol-4-yl-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid ethyl ester (0.073 g, 0.182 mmol) was dissolved in THF (2 mL), H2O (0.75 mL) and MeOH (0.75 mL) and LiOH.H2O (0.040 g, 0.953 mmol) was added. The reaction was stirred at room temperature and monitored by analytical LCMS. When no starting material remained the reaction was diluted with H2O and EtOAc and citric acid was added until pH 3 was reached. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic portions were washed with H2O, dried over MgSO4 and concentrated. The residue was purified via silica gel chromatography (0-5% MeOH in DCM) to give the title compound.

後処理

  1. additionwas added until pH 3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic portions were washed with H2O
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified via silica gel chromatography (0-5% MeOH in DCM)

出典と根拠

ORDレコード
ord-ada47c57b94c46cab51f951f84665c28
出典データセット
uspto-grants-2015_04
特許番号
US09000025B2

反応ノート

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