Lithium Hydroxide → HCID 59627762, compound

HRID 2406893Notes

Reaction equation

HRID 2406893 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[CH:8]=[C:9]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[O:13][C:12]2=[O:20])[CH:10]=1)=[O:4].[Li+].[OH-]>CN(C=O)C>[CH3:27][C:24]1[CH:23]=[CH:22][C:21]([C:7]2[CH:8]=[C:9]([N:11]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[O:13][C:12]3=[O:20])[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59627760HCID 59627760, compound

Product 1

HCID 59627762HCID 59627762, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

The 4′-methyl-5-(2-oxo-benzooxazol-3-yl)-biphenyl-3-carboxylic acid methyl ester from step 1 was dissolved in DMF (6 mL) and LiOH (500 mg, excess) was added. The reaction mixture was stirred at 120° C. overnight and then cooled to room temperature and partitioned between dichloromethane and saturated aqueous citric acid solution. The organic layer was concentrated under reduced pressure to give crude 4′-methyl-5-(2-oxo-benzooxazol-3-yl)-biphenyl-3-carboxylic acid, which was used directly in the next step.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between dichloromethane and saturated aqueous citric acid solution
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a652c804ff0c45cb8b52e69277692ee5
Source dataset
uspto-grants-2014_08
Patent number
US08809402B2

Reaction notes

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