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

HRID 56248

반응식

HRID 56248 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7e55147ce4b0467baec2efdab69a220d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

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