Acetic Acid → methyl (Z)-3-acetamido-2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-2-heptenoate

HRID 1622975Notes

Reaction equation

HRID 1622975 reaction equation
C1(C)C=CC=CC=1.[C:8]([OH:11])(=O)[CH3:9].[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[N:25]=[CH:24][C:23]([CH2:26][CH:27]([C:32](=O)[CH2:33][CH2:34][CH2:35][CH3:36])[C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=1)#[N:13].C([O-])(=O)C.[NH4+:42]>CCCCCC.CC(C)=O>[C:8]([NH:42]/[C:32](/[CH2:33][CH2:34][CH2:35][CH3:36])=[C:27](/[CH2:26][C:23]1[CH:24]=[N:25][C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:12]#[N:13])=[CH:21][CH:22]=1)\[C:28]([O:30][CH3:31])=[O:29])(=[O:11])[CH3:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 517165Ammonium AcetateHCID 67008908Methyl 2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-oxoheptanoate

Product 1

HCID 86667259methyl (Z)-3-acetamido-2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-2-heptenoateYield 25%

Reagents, catalysts & solvents 1

HCID 21880519Acetone hexaneSolvent

Conditions

Temperature
0 °C

Procedure

Process 2: A toluene (50 mL)-acetic acid (7 mL) solution of methyl 2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-oxoheptanoate (3.50 g, 10.0 mmol) and ammonium acetate (23.2 g, 300 mmol) was refluxed for 1 hour under heating. The solvent was distilled off and the residues were added anhydrous acetic acid (51.2 g) and acetic acid (5.7 g) under room temperature, and the reaction solution was stirred at 0° C. for 30 minutes, and then stirred at 70° C. for 1.5 hours. The reaction solution was added aqueous sodium bicarbonate, and extracted with chloroform. The organic layer was combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residues obtained were subjected to silica gel column chromatography (hexane/acetone=5:1), to obtain methyl(Z)-3-acetamido-2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-2-heptenoate (0.975 g, 25%) as a pale yellow oil.

Workup

  1. temperatureunder heating
  2. distillationThe solvent was distilled off
  3. additionthe residues were added anhydrous acetic acid (51.2 g) and acetic acid (5.7 g) under room temperature
  4. stirringstirred at 70° C. for 1.5 hours
  5. additionThe reaction solution was added aqueous sodium bicarbonate
  6. extractionextracted with chloroform
  7. washwashed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residues obtained

Sources & evidence

ORD record
ord-5c4a5472bb1f406398dd388e107c6c7d
Source dataset
uspto-grants-2014_07
Patent number
US08778954B2

Reaction notes

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