Lithium hydroxide, monohydrate → 4'-Methyl-5-thiazol-2-yl-biphenyl-3-carboxylic acid

HRID 1888899Notes

Reaction equation

HRID 1888899 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH:8]=[C:9]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[CH:10]=1)=[O:4].O[Li].O>C1COCC1.O>[CH3:22][C:19]1[CH:18]=[CH:17][C:16]([C:7]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 594325714'-Methyl-5-thiazol-2-yl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 594325694'-Methyl-5-thiazol-2-yl-biphenyl-3-carboxylic acidYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4′-methyl-5-thiazol-2-yl-biphenyl-3-carboxylic acid methyl ester (0.310 g, 1 mmol) in THF (10 mL) was added a solution of LiOH—H2O (1.2 mmol) in H2O (15 mL) at 0° C. The reaction was allowed to warm to room temperature and was stirred until the disappearance of the ester was confirmed by TLC. Solvent was removed under reduced pressure and the aqueous solution was acidified to pH=2 by dropwise addition of 10% aqueous HCl. The resulting solid was collected by filtration and dried to yield 4′-Methyl-5-thiazol-2-yl-biphenyl-3-carboxylic acid (0.22 g, 75%). MS (M+H)=296.

Workup

  1. customSolvent was removed under reduced pressure
  2. additionthe aqueous solution was acidified to pH=2 by dropwise addition of 10% aqueous HCl
  3. filtrationThe resulting solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-861fb8af27184e20b2cba05d24d2e353
Source dataset
uspto-grants-2013_08
Patent number
US08501933B2

Reaction notes

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