Acetic Acid → (Z)-ethyl 3-(2-(tert-butoxycarbonylamino)ethylamino)-3-(2,4-dimethoxyphenyl)acrylate

HRID 1056515ノート

反応式

HRID 1056515 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[NH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].C(O)(=O)C>C(O)C>[C:25]([O:24][C:23]([NH:22][CH2:21][CH2:20][NH:19]/[C:11](/[C:4]1[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[O:2][CH3:1])=[CH:12]\[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:29])([CH3:28])([CH3:27])[CH3:26]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 187201N-BOC-ethylenediamineHCID 2758464Ethyl 3-(2,4-dimethoxyphenyl)-3-oxopropanoate

生成物 1

HCID 86701198(Z)-ethyl 3-(2-(tert-butoxycarbonylamino)ethylamino)-3-(2,4-dimethoxyphenyl)acrylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of ethyl 3-(2,4-dimethoxyphenyl)-3-oxopropanoate (41.91 g, 166 mmol), tert-butyl 2-aminoethylcarbamate (54.7 g, 342 mmol), and acetic acid (16.14 g, 269 mmol) in ethanol (180 mL) was heated at reflux for 5.3 h. After removal of most of the solvent by rotary evaporation, the resulting oil was partitioned between EtOAc (ca. 300 mL) and 10% (w/v) aq. ammonium chloride. The EtOAc layer was separated and then washed with water, 10% (w/v) aq. ammonium chloride (3 mL), and brine (10 mL). The EtOAc layer was washed with sat. aq. sodium bicarbonate, brine (6 mL) was added, and the emulsion was allowed to settle. The EtOAc layer was finally washed with brine and dried over sodium sulfate. Evaporation of the EtOAc layer's volatile components afforded a viscous, amber taffy (62.3 g, 95%). This crude product was used without further purification.

後処理

  1. temperatureat reflux for 5.3 h
  2. customAfter removal of most of the solvent
  3. customby rotary evaporation
  4. customthe resulting oil was partitioned between EtOAc (ca. 300 mL) and 10% (w/v) aq. ammonium chloride
  5. customThe EtOAc layer was separated
  6. washwashed with water, 10% (w/v) aq. ammonium chloride (3 mL), and brine (10 mL)
  7. washThe EtOAc layer was washed with sat. aq. sodium bicarbonate, brine (6 mL)
  8. additionwas added
  9. washThe EtOAc layer was finally washed with brine
  10. dry with materialdried over sodium sulfate
  11. customEvaporation of the EtOAc
  12. customafforded a viscous, amber taffy (62.3 g, 95%)
  13. customThis crude product was used without further purification

出典と根拠

ORDレコード
ord-55cca8096fb1400ea0362a9c920933c2
出典データセット
uspto-grants-2016_07
特許番号
US09399626B2

反応ノート

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