Pyridine → (Z)-methyl 3-(3-(3-fluorophenyl)propanamido)but-2-enoate

HRID 56248

反応式

HRID 56248 の反応式
[NH2:1]/[C:2](/[CH3:8])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.[F:15][C:16]1[CH:17]=[C:18]([CH2:22][CH2:23][C:24](Cl)=[O:25])[CH:19]=[CH:20][CH:21]=1>C(Cl)Cl>[F:15][C:16]1[CH:17]=[C:18]([CH2:22][CH2:23][C:24]([NH:1]/[C:2](/[CH3:8])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5])=[O:25])[CH:19]=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 643918Methyl 3-aminocrotonateHCID 189935013-(3-Fluorophenyl)propanoyl chloride

生成物 1

HCID 90023034(Z)-methyl 3-(3-(3-fluorophenyl)propanamido)but-2-enoate収率 51%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (Z)-methyl 3-aminobut-2-enoate (1.70 g, 14.8 mmol) and pyridine (1.30 g, 16.4 mmol) in DCM (25 mL) was added a solution of 3-(3-fluorophenyl)propanoyl chloride (2.77 g, 14.8 mmol) in DCM (5 mL) dropwise with stirring. At the end of addition, the mixture was stirred further at rt for 1 h. It was then washed with brine (50 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=3:1) to give the title compound as a white solid (2.00 g, 51%).

後処理

  1. additionAt the end of addition
  2. stirringthe mixture was stirred further at rt for 1 h
  3. washIt was then washed with brine (50 mL×3)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=3:1)

出典と根拠

ORDレコード
ord-7e55147ce4b0467baec2efdab69a220d
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

関連ノート

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