Cesium carbonate → {6-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid

HRID 490766ノート

反応式

HRID 490766 の反応式
Cl[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH:18]([CH3:20])[CH3:19].C([O:23][C:24](=[O:36])[CH2:25][C:26]1[C:27]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:28]=2[S:29][CH:30]=1)C.C([O-])([O-])=O.[Cs+].[Cs+].[OH-].[Na+]>C(#N)C.C(O)C>[CH:18]([C:4]1[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[S:7][C:3]=1[CH2:2][O:35][C:32]1[CH:33]=[CH:34][C:27]2[C:26]([CH2:25][C:24]([OH:36])=[O:23])=[CH:30][S:29][C:28]=2[CH:31]=1)([CH3:20])[CH3:19]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 57431998(6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl esterHCID 589340885-Chloromethyl-4-isopropyl-2-[4-(trifluoromethyl)phenyl]thiazole

生成物 1

HCID 10368353{6-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 5-chloromethyl-4-isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole (100 mg, 0.31 mmol) and (6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (75 mg, 0.31 mmol) in acetonitrile (3 mL) is added Cs2CO3 (200 mg, 0.62 mmol). The mixture is stirred at room temperature overnight, ethanol (1 mL) is added, followed by NaOH (5 N, 1.0 mL). The mixture is heated at 50° C. for 2 hrs, solvent is evaporate, the residue is diluted with water, acidified by 5N HCl and extracted with ethyl acetate. Concentration and reversed phase HPLC purification yields the title product. MS (ES): 490.0 (M+−1).

後処理

  1. temperatureThe mixture is heated at 50° C. for 2 hrs
  2. customsolvent is evaporate
  3. additionthe residue is diluted with water
  4. extractionextracted with ethyl acetate
  5. concentrationConcentration
  6. customphase HPLC purification

出典と根拠

ORDレコード
ord-693ccb0ba6414c359f00c99c86af5c81
出典データセット
uspto-grants-2009_05
特許番号
US07528160B2

反応ノート

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