Lithium Hydroxide → HCID 16074694, compound

HRID 2193918Notes

Reaction equation

HRID 2193918 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:4].[Li+].[OH-]>C1COCC1.CO.O>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[C:17]([N:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:9]1[CH:8]=[C:7]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2])=[O:26]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 20775752HCID 20775752, compound

Product 1

HCID 16074694HCID 16074694, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

3-[(2,4-Dichloro-benzoyl)-phenyl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (55 mg, 0.11 mmol) was dissolved in a mixture of THF-MeOH—H2O (3:2:1) (15 mL) and then 0.66 ml of LiOH 1N was added to it. After 60 min of stirring at room temperature, solvents were removed and then partitioned between 15 ml of H2O, 4 ml of KHSO4 5% and 15 ml of EtOAc. The organic layer was separated and the aqueous phase was washed twice with ethyl acetate (2×10 mL). The combined ethyl acetate layer was dried (MgSO4), concentrated and the residue was purified by preparative chromatography (10% MeOH/CH2Cl2) to obtain 32 mg (60%) of 3-[(2,4-Dichloro-benzoyl)-phenyl-amino]-5-phenyl-thiophene-2-carboxylic acid. NMR 1H (DMSO, 400 MHz): Rotamer: 7.75 ppm (d, 1H, Haro); 7.68 ppm (2H, Haro); 7.53 ppm (d, Haro, minor rotamer); 7.51-7.23 ppm (m, 11H, Haro, minor rotamer); 7.17 ppm (Haro, minor rotamer).

Workup

  1. customsolvents were removed
  2. custompartitioned between 15 ml of H2O, 4 ml of KHSO4 5% and 15 ml of EtOAc
  3. customThe organic layer was separated
  4. washthe aqueous phase was washed twice with ethyl acetate (2×10 mL)
  5. dry with materialThe combined ethyl acetate layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue was purified by preparative chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-5bbe2848af9341a9a1ba05fbc267feb1
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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