Water → Methyl 4-(2-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorophenyl)acetyl)-1,2,5-trimethyl-1H-pyrrole-3-carboxylate

HRID 1091739ノート

反応式

HRID 1091739 の反応式
IC.[CH2:3]([O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([C:14]2[CH:15]=[C:16]([CH2:21][C:22]([C:24]3[C:25]([C:31]([O:33][CH3:34])=[O:32])=[C:26]([CH3:30])[NH:27][C:28]=3[CH3:29])=[O:23])[CH:17]=[CH:18][C:19]=2[F:20])=[O:13])[CH2:8][CH2:7]1)[CH3:4].[C:35](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:3]([O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([C:14]2[CH:15]=[C:16]([CH2:21][C:22]([C:24]3[C:25]([C:31]([O:33][CH3:34])=[O:32])=[C:26]([CH3:30])[N:27]([CH3:35])[C:28]=3[CH3:29])=[O:23])[CH:17]=[CH:18][C:19]=2[F:20])=[O:13])[CH2:8][CH2:7]1)[CH3:4]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57791805methyl 4-(2-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorophenyl)acetyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate

生成物 1

HCID 57791827Methyl 4-(2-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorophenyl)acetyl)-1,2,5-trimethyl-1H-pyrrole-3-carboxylate収率 77%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Iodomethane (0.056 mL, 0.90 mmol) was added to methyl 4-(2-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorophenyl)acetyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (53) (0.200 g, 0.45 mmol) and potassium carbonate (0.249 g, 1.80 mmol) in DMF (10 mL). The resulting suspension was stirred at room temperature for 2 hours. The reaction mixture was poured into water (75 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (50 mL) and saturated brine (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford the desired material as a yellow gum (0.158 g, 77% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.14 (3H, t), 1.43-1.65 (2H, m), 1.72 (1H, m), 1.85 (1H, m), 2.05 (3H, s), 2.38 (3H, s), 3.06 (1H, m), 3.32 (3H, s), 3.45 (5H, m), 3.74 (3H, s), 3.91 (2H, s), 3.99 (1H, m), 6.93 (1H, t), 7.08 (1H, m), 7.17 (1H, m); m/z (LC-MS, ESI+), RT=2.15 min (M+H=459.36).

後処理

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic layers were washed with water (50 mL) and saturated brine (50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product
  7. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 100% ethyl acetate in isohexane
  8. customPure fractions were evaporated to dryness

出典と根拠

ORDレコード
ord-b4b97d01956e4a99a97c49878b28c1f9
出典データセット
uspto-grants-2012_03
特許番号
US08129380B2

反応ノート

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