Water → HCID 67307990, compound

HRID 404127Notes

Reaction equation

HRID 404127 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[CH2:9]Br.C(=O)([O-])[O-].[K+].[K+].[CH3:26][O:27][C:28](=[O:34])[C@H:29]([CH:31]([CH3:33])[CH3:32])[NH2:30].O>C(#N)C>[CH3:32][CH:31]([CH3:33])[CH:29]([N:30]1[CH2:2][C:3]2[C:8](=[CH:7][CH:6]=[C:5]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[CH:4]=2)[CH2:9]1)[C:28]([O:27][CH3:26])=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 94285Valine methyl esterHCID 673071543,4-bis(Bromomethyl)-4'-nitrobiphenyl

Product 1

HCID 67307990HCID 67307990, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound of example 671 (3 g, 7.79 mmol) was taken in acetonitrile and to the reaction mixture, potassium carbonate (3.25 g, 23.37 mmol) was added followed by the addition of valine methyl ester (1.56 g, 9.35 mmol). The reaction mixture was refluxed for about 16 h and water was added to quench the reaction. The aqueous mixture was extracted with ethyl acetate to obtain a crude material, which was purified using column chromatography (silicagel, 30% ethyl acetate in petroleum ether).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for about 16 h
  3. customto quench
  4. customthe reaction
  5. extractionThe aqueous mixture was extracted with ethyl acetate

Sources & evidence

ORD record
ord-836010156a004d728a8f4cde327f0724
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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