Pyridine → methyl 2-(N-benzyl-4-nitrobenzamido)-2-phenylacetate

HRID 1951575

反応式

HRID 1951575 の反応式
[CH2:1]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[N+:26]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)([O-:28])=[O:27]>ClCCl>[CH2:1]([N:8]([CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11])[C:33](=[O:34])[C:32]1[CH:31]=[CH:30][C:29]([N+:26]([O-:28])=[O:27])=[CH:37][CH:36]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 3699844Methyl 2-(benzylamino)-2-phenylacetate

生成物 1

HCID 57465368methyl 2-(N-benzyl-4-nitrobenzamido)-2-phenylacetate収率 96.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

to a solution of methyl 2-(benzylamino)-2-phenylacetate (4.818 g, 18.9 mmol) and pyridine (15.3 ml, 189 mmol) in 75 mL dichloromethane cooled by an ice bath was added 4-nitrobenzoyl chloride (3.50 g, 18.9 mmol) all at once. The cold bath was removed and the reaction stirred to room temperature. The reaction was stirred at room temperature for four hours then concentrated under reduced pressure, taken up in 100 mL heptane and concentrated under reduced pressure. The concentrate was partitioned between 100 mL dichloromethane and 100 mL water. The organic separation was washed with 50 mL brine then stirred over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a colorless oil. The product was purified by chromatography on silica, eluting with 10-30% ethyl acetate in hexane to afford a colorless foamy solid (7.37 g, 96%). ESI+ m/z=405.1 [MH]+.

後処理

  1. customThe cold bath was removed
  2. stirringThe reaction was stirred at room temperature for four hours
  3. concentrationthen concentrated under reduced pressure
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was partitioned between 100 mL dichloromethane and 100 mL water
  6. customThe organic separation
  7. washwas washed with 50 mL brine
  8. stirringthen stirred over magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under reduced pressure
  11. customto afford a colorless oil
  12. customThe product was purified by chromatography on silica
  13. washeluting with 10-30% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-b6a573e29af74cc0b7b8e84e531529b8
出典データセット
uspto-grants-2013_03
特許番号
US08404722B2

関連ノート

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