Sodium Hydroxide → 6-Chloro-5-[4-(1-hydroxy-2-methylpropan-2-yl)-3-methoxyphenyl]-1H-indole-3-carboxylic acid

HRID 338382ノート

反応式

HRID 338382 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13]C)=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[CH2:22][OH:23])=[C:17]([O:26][CH3:27])[CH:16]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[CH2:22][OH:23])=[C:17]([O:26][CH3:27])[CH:16]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 86698724Methyl 6-chloro-5-(4-(1-hydroxy-2-methylpropan-2-yl)-3-methoxyphenyl)-1H-indole-3-carboxylate

生成物 1

HCID 717659536-Chloro-5-[4-(1-hydroxy-2-methylpropan-2-yl)-3-methoxyphenyl]-1H-indole-3-carboxylic acid収率 75.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

A mixture of the methyl 6-chloro-5-(4-(1-hydroxy-2-methylpropan-2-yl)-3-methoxyphenyl)-1H-indole-3-carboxylate (25 mg, 0.064 mmol), 2.4 ml of methanol (2.4 mL), and 0.8 mL of 1M aqueous solution of sodium hydroxide (0.8 mL, 0.8 mmol) was stirred at 70° C. for 24 hours—the starting material is consumed by TLC and LCMS. The reaction mixture was cooled to room temperature, diluted with 1M solution of potassium bisulfate (1 mL) and the obtained mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic extract was washed with brine, dried over anhydrous magnesium sulfate and loaded on silica gel. A silica gel column was equilibrated with 30% ethyl acetate in heptane. Chromatography on this column, eluting with a solution of 3% of acetic acid and 30% of ethyl acetate in heptane gave the title compound (18 mg, 73% yield). MS (ES−) 372.1 (M−H)− Retention time:

後処理

  1. customis consumed by TLC and LCMS
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additiondiluted with 1M solution of potassium bisulfate (1 mL)
  4. concentrationthe obtained mixture was concentrated
  5. customThe residue was partitioned between ethyl acetate and water
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. washChromatography on this column, eluting with a solution of 3% of acetic acid and 30% of ethyl acetate in heptane

出典と根拠

ORDレコード
ord-9d96ca68672c47c7b97c7a5f300a75a2
出典データセット
uspto-grants-2014_11
特許番号
US08889730B2

反応ノート

読み込み中…