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Potassium Hydroxide → 3-(2-(4'-(6-Carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)propanoic acid

HRID 1930151
ノート
印刷プレビュー

反応式

HRID 1930151 の反応式
[OH-].[K+].[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[O:26])=[CH:20][C:19]=3[Cl:35])=[CH:14][CH:13]=2)[C:9]([CH3:36])=[N:8][C:7]=1[CH3:37])(=[O:5])[NH2:4]>CC(O)(C)C>[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:26])=[CH:20][C:19]=3[Cl:35])=[CH:14][CH:13]=2)[C:9]([CH3:36])=[N:8][C:7]=1[CH3:37])(=[O:5])[NH2:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 59627636Ethyl 3-(2-(4'-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)propanoate2 回

生成物 1

HCID 672857433-(2-(4'-(6-Carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)propanoic acid収率 15.5%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
45 °C

実験手順

Potassium hydroxide (131 mg, 2.34 mmol) was added in one portion to ethyl 3-(2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)propanoate (Intermediate 16-1; 386.5 mg, 0.78 mmol) in t-BuOH (5038 μL) at RT. The resulting solution was stirred at 45° C. for 5 hours a precipitate formed. The reaction mixture was quenched with 2M HCl (5 mL), The reaction mixture was evaporated to dryness and redissolved in water (10 mL), and filtered through nylon, washed with water and dried under vacuum. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 50 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 3-(2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)propanoic acid (56.4 mg, 15.47%) as a white solid.

後処理

  1. customformed
  2. customThe reaction mixture was quenched with 2M HCl (5 mL)
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutionredissolved in water (10 mL)
  5. filtrationfiltered through nylon
  6. washwashed with water
  7. customdried under vacuum
  8. customThe crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 50 mm diameter, 150 mm length)
  9. additionFractions containing the desired compound
  10. customwere evaporated to dryness

出典と根拠

ORDレコード
ord-e92d327c4e244c67984f2c43e255911d
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08188092B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート