Dimethylformamide → alpha-Cyano-m-phenoxybenzyl 2-(2-isoindolinyl)-3-methylbutanoate

HRID 1447951Notes

Reaction equation

HRID 1447951 reaction equation
[CH3:1][N:2]([CH:4]=O)[CH3:3].[C:6](=[O:9])([O-])[O-:7].[K+].[K+].S(O[CH:17]([C:31]#[N:32])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=1)(=O)(=O)C>C1COCC1.CCOCC>[CH2:4]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:3][N:2]1[CH:1]([CH:25]([CH3:30])[CH3:26])[C:6]([O:7][CH:17]([C:31]#[N:32])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=1)=[O:9]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 20482835alpha-Cyano-m-phenoxybenzyl mesylate

Product 1

HCID 54247008alpha-Cyano-m-phenoxybenzyl 2-(2-isoindolinyl)-3-methylbutanoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the above acid (1 g, 4.6 mmol) in 12 ml THF is added 8 ml of DMF and potassium carbonate (0.63 g, 5 mmol) followed by α-cyano-m-phenoxybenzyl mesylate (1.31 g, 5 mmol). The reaction mixture is stirred, under nitrogen, at RT for 20 hours. The reaction mixture is then diluted with ether. The organic layer is washed with water and brine, dried and solvent removed under vacuum. The residue is purified by prep. TLC to give α-cyano-m-phenoxybenzyl 2-(2-isoindolinyl)-3-methylbutanoate.

Workup

  1. washThe organic layer is washed with water and brine
  2. customdried
  3. customsolvent removed under vacuum
  4. customThe residue is purified by prep

Sources & evidence

ORD record
ord-444f27ca839849f490a64467203c0940
Source dataset
uspto-grants-1979_12
Patent number
US04178293

Reaction notes

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