Methyl Acrylate → 3-[2-(tert-Butoxycarbonylamino-methyl)-phenyl]-acrylic acid methyl ester

HRID 1371521ノート

反応式

HRID 1371521 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)([CH3:4])([CH3:3])[CH3:2].[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19]>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:22][O:21][C:17](=[O:20])[CH:18]=[CH:19][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:16]

参加物

6

反応物 2

HCID 7294Methyl AcrylateHCID 70183002-Bromo-N-(tert-butoxycarbonyl)benzylamine

生成物 1

HCID 692195883-[2-(tert-Butoxycarbonylamino-methyl)-phenyl]-acrylic acid methyl ester

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To compound of Step A (161.0 g, 561.8 mmol) in DMF (800 mL) is added methyl acrylate (58.0 g, 674.2 mmol), TEA (170.5 g, 1685.4 mmol) and dichlorobis(triphenylphosphine)palladium(II) (7.9 g, 11.2 mmol). The mixture is heated at 80° C. for about 32 hours. The mixture is cooled, diluted with 1000 mL of EtOAc and washed with 10% aqueous sodium bisulfate. The aqueous portion is extracted three times with EtOAc and the combined organics are dried (Na2SO4) and concentrated to dryness. The residue is dissolved in a small amount of DCM and filtered through 7 inch of silica gel in a 2 L sintered glass funnel eluting with 25% EtOAc/hexanes. The eluent is concentrated to dryness and recrystallized from EtOAc/hexanes to afford about 116.9 g (71%) of Step B compound.

後処理

  1. temperatureThe mixture is cooled
  2. washwashed with 10% aqueous sodium bisulfate
  3. extractionThe aqueous portion is extracted three times with EtOAc
  4. dry with materialthe combined organics are dried (Na2SO4)
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue is dissolved in a small amount of DCM
  7. filtrationfiltered through 7 inch of silica gel in a 2 L sintered glass funnel
  8. washeluting with 25% EtOAc/hexanes
  9. concentrationThe eluent is concentrated to dryness
  10. customrecrystallized from EtOAc/hexanes
  11. customto afford about 116.9 g (71%) of Step B compound

出典と根拠

ORDレコード
ord-8afd36daa8f14f39b41258846cf77805
出典データセット
uspto-grants-2007_01
特許番号
US07157463B2

反応ノート

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