3-Bromo-5-ethoxy-4-hydroxybenzaldehyde → 4-(3-bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid (1S)-[1-(4-methoxy-phenyl)-ethyl]-amide

HRID 910763Notes

Reaction equation

HRID 910763 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12](=[O:17])[CH:13]=[C:14]([NH2:16])[CH3:15])[CH3:10])=[CH:5][CH:4]=1.[Br:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([O:28][CH2:29][CH3:30])[C:26]=1[OH:27])[CH:22]=O.[CH2:31]([CH:34]1[CH2:39][C:38](=[O:40])[CH2:37][C:36](=O)[CH2:35]1)[CH2:32][CH3:33]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]([NH:11][C:12]([C:13]2[CH:22]([C:21]3[CH:24]=[C:25]([O:28][CH2:29][CH3:30])[C:26]([OH:27])=[C:19]([Br:18])[CH:20]=3)[C:37]3[C:38](=[O:40])[CH2:39][CH:34]([CH2:31][CH2:32][CH3:33])[CH2:35][C:36]=3[NH:16][C:14]=2[CH3:15])=[O:17])[CH3:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehydeHCID 27372245-Propylcyclohexane-1,3-dioneHCID 67417518(s)-3-Amino-but-2-enoic acid [1-(4-methoxy-phenyl)-ethyl]-amide

Product 1

HCID 674194224-(3-bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid (1S)-[1-(4-methoxy-phenyl)-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (S)-3-amino-but-2-enoic acid [1-(4-methoxy-phenyl)-ethyl]-amide (10 g), 3-bromo-5-ethoxy-4-hydroxy-benzaldehyde (10.4 g) and 5-propylcyclohexane-1,3-dione (6.5 g) in ethanol (150 ml) was stirred at 80° C. for 18 hr. The mixture was concentrated in vacuo. The residue was dissolved in toluene (100 ml) and dichloromethane (50 ml) and evaporated until a precipitated formed. The solid obtained was then crystallized in EtOAc.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in toluene (100 ml)
  3. customdichloromethane (50 ml) and evaporated until a precipitated
  4. customformed
  5. customThe solid obtained
  6. customwas then crystallized in EtOAc

Sources & evidence

ORD record
ord-a429293d35a64bc08d2dab2e8e49d804
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

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