Lithium hydroxide, monohydrate → 4'-Methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid

HRID 736902Notes

Reaction equation

HRID 736902 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[CH:8]=[C:9]([N:11]2[C:15]([CH3:16])=[N:14][N:13]=[N:12]2)[CH:10]=1)=[O:4].O[Li].O>C1COCC1.O>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([C:7]2[CH:8]=[C:9]([N:11]3[C:15]([CH3:16])=[N:14][N:13]=[N:12]3)[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 578509314'-Methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 578509354'-Methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4′-methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid methyl ester (1 mmol, 308 mg) in 10 ml of THF was added a solution of LiOH.H2O (5 mmol, 210 mg) in 2 mL of water. The reaction mixture was heated to reflux for 3.5 hours and then cooled to room temperature. Solvent was removed under reduced pressure and the liquid residue was pH adjusted to 2.0 by addition of 2N aqueous HCl solution. The mixture was extracted with ethyl acetate and the combined ethyl acetate layers were dried over anhydrous Na2SO4 and concentrated in vacuo to give 4′-methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid as white solid (279 mg, 95% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. customSolvent was removed under reduced pressure
  4. additionthe liquid residue was pH adjusted to 2.0 by addition of 2N aqueous HCl solution
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialthe combined ethyl acetate layers were dried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-143b1c42b9b345a59519d45174a16bff
Source dataset
uspto-grants-2009_09
Patent number
US07595405B2

Reaction notes

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