Ethyl Acetate → HCID 136146786, compound

HRID 1674124Notes

Reaction equation

HRID 1674124 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([C:21](=O)[CH2:22][CH2:23][CH2:24][CH3:25])[C:17](OC)=[O:18])=[CH:11][CH:10]=1)#[N:2].[C:27]1([CH2:33][CH2:34][C:35](=[NH:37])[NH2:36])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C[O-].[Na+].CO.C(OCC)(=O)C>CO.O>[CH2:22]([C:21]1[N:37]=[C:35]([CH2:34][CH2:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:36][C:17](=[O:18])[C:16]=1[CH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:4]2[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:14][CH:13]=1)[CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 424661HCID 424661, compoundHCID 10807723Methyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoateHCID 23694274Sodium methanolate methanol

Product 1

HCID 136146786HCID 136146786, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoate (0.70 g) and 3-phenylpropanimidamide (0.63 g) in methanol (10 mL) was added 28% sodium methoxide-methanol solution (1.7 mL), and the mixture was stirred at room temperature for 24 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow viscous substance (0.71 g, 79%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e923a753bf0b4429aea2b08473a42143
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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