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

HRID 77540Notes

Reaction equation

HRID 77540 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6999e32cbefb4b8fa798b45172784c2f
Source dataset
uspto-grants-2014_09
Patent number
US08841314B2

Reaction notes

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