Dimethylformamide → HCID 18870964, compound

HRID 1447950Notes

Reaction equation

HRID 1447950 reaction equation
CN(C=O)C.[NH2:6][C@H:7]([C:11]([OH:13])=[O:12])[CH:8]([CH3:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+].Br[CH:21](Br)[C:22]1[C:23]([CH3:28])=[CH:24][CH:25]=[CH:26][CH:27]=1>O.CCOCC>[CH2:28]1[C:23]2[C:22](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][N:6]1[CH:7]([CH:8]([CH3:10])[CH3:9])[C:11]([OH:13])=[O:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6287L-ValineHCID 11430Potassium CarbonateHCID 6390401-(Dibromomethyl)-2-methylbenzene

Product 1

HCID 18870964HCID 18870964, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To 20 ml DMF is added valine (1.17 g, 10 mmol) and potassium carbonate (5.5 g, 40 mmol) followed by α,α-dibromo-o-xylene (2.63 g, 10 mmol). The reaction mixture is stirred for about 20 hours at RT under nitrogen and then poured into ether and water. The aqueous layer is separated, acidified to about pH 3 with aqueous HCl and extracted thoroughly with ether. The organic layer is washed with water and brine, dried and solvent removed under vacuum to give 2-(2-isoindolinyl)-3-methylbutanoic acid.

Workup

  1. customThe aqueous layer is separated
  2. extractionextracted thoroughly with ether
  3. washThe organic layer is washed with water and brine
  4. customdried
  5. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-5ecb5694f6784986bd734327c06cd335
Source dataset
uspto-grants-1979_12
Patent number
US04178293

Reaction notes

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