Ethyl 3-chloro-3-oxopropionate → Methyl 3-{cyclopropyl[3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate

HRID 2364529ノート

反応式

HRID 2364529 の反応式
[CH:1]1([NH:4][C:5]2[C:6]([C:19]([O:21][CH3:22])=[O:20])=[N:7][CH:8]=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:10]=2)[CH2:3][CH2:2]1.Cl[C:24](=[O:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)(O)[O-].[Na+]>ClCCl>[CH:1]1([N:4]([C:24](=[O:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:5]2[C:6]([C:19]([O:21][CH3:22])=[O:20])=[N:7][CH:8]=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:10]=2)[CH2:2][CH2:3]1

参加物

5

反応物 3

HCID 118931Ethyl 3-chloro-3-oxopropionateHCID 516892Sodium BicarbonateHCID 69481047Methyl 3-(cyclopropylamino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate

生成物 1

HCID 69480475Methyl 3-{cyclopropyl[3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate収率 88.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of methyl 3-(cyclopropylamino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (234 mg, 0.78 mmol) and ethyl 3-chloro-3-oxopropanoate (0.13 mL, 90%, 1.0 mmol) was heated at 85° C. for 3 hours. Upon cooling to room temperature, dichloromethane and saturated aqueous sodium bicarbonate were added and the layers separated. The organic layer was washed with brine. The aqueous layers were extracted with dichloromethane and the combined organics dried over sodium sulfate. Filtration and concentration followed by silica gel chromatography provided methyl 3-{cyclopropyl[3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (285 mg, 88%) as an oil.

後処理

  1. customthe layers separated
  2. washThe organic layer was washed with brine
  3. extractionThe aqueous layers were extracted with dichloromethane
  4. dry with materialthe combined organics dried over sodium sulfate
  5. filtrationFiltration and concentration

出典と根拠

ORDレコード
ord-4dc7726931264c4d8ea68a22ff865ab1
出典データセット
uspto-grants-2014_04
特許番号
US08691991B2

反応ノート

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