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

HRID 338382노트

반응식

HRID 338382 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
70 °C

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-9d96ca68672c47c7b97c7a5f300a75a2
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889730B2

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