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Sodium Hydroxide → [(3-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-pyrazol-5-yl)oxy]acetic acid

HRID 535013
ノート
印刷プレビュー

反応式

HRID 535013 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:23]=[C:22]([O:24][CH2:25][C:26]([O:28]C)=[O:27])[N:21]([CH3:30])[N:20]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1.CO>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:23]=[C:22]([O:24][CH2:25][C:26]([OH:28])=[O:27])[N:21]([CH3:30])[N:20]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 86663403Methyl [(3-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-pyrazol-5-yl)oxy]acetate

生成物 1

HCID 66792875[(3-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-pyrazol-5-yl)oxy]acetic acid収率 54.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran
溶媒

実験手順

A mixture of methyl [(3-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-pyrazol-5-yl)oxy]acetate (0.573 g, 1.38 mmol) and 1 M sodium hydroxide solution (5 mL) in tetrahydrofuran (20 mL) and methanol (20 mL) was stirred at room temperature for 3 h. Solvent was removed and 1 M hydrochloric acid solution added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to purify the residue by HPLC (Gilson Preparative HPLC System; column: YMC Combiprep ODS-A, S-5 μm, 50×20 mm; solvent: A; water containing 0.1% TFA, B; acetonitrile containing 0.1% TFA; gradient cycle: 0.00 min (A/B=90/10), 1.00 min (A/B=90/10), 4.20 min (A/B=10/90), 5.40 min (A/B=10/90), 5.50 min (A/B=90/10), 5.60 min (A/B=90/10); flow rate: 25 mL/min; detect: UV 220 nm). Solvent was removed to afford a solid (0.3 g, 54%).

後処理

  1. customSolvent was removed
  2. addition1 M hydrochloric acid solution added to the mixture
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto purify the residue by HPLC (Gilson Preparative HPLC System
  9. custom0.00 min
  10. custom1.00 min
  11. custom4.20 min
  12. custom5.40 min
  13. custom5.50 min
  14. custom5.60 min
  15. customSolvent was removed

出典と根拠

ORDレコード
ord-f3e0441884674273873ea154272719f5
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08853215B2

反応ノート

読み込み中…

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