Water → HCID 57770868, compound

HRID 1669892Notes

Reaction equation

HRID 1669892 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[N:8][N:9]([C:14]2[CH:15]=[C:16]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[CH:17]=[C:18]([C:20]([O:22]C)=[O:21])[CH:19]=2)[C:10]=1[CH:11]([CH3:13])[CH3:12])=[O:5])C.O.O[Li].O>C1COCC1>[C:20]([C:18]1[CH:19]=[C:14]([N:9]2[C:10]([CH:11]([CH3:13])[CH3:12])=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[N:8]2)[CH:15]=[C:16]([C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)[CH:17]=1)([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57770808HCID 57770808, compound

Product 1

HCID 57770868HCID 57770868, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 5-isopropyl-1-(5-methoxycarbonyl-4′-methyl-biphenyl-3-yl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester from step 1 was dissolved in THF (7 mL) and water (4 mL) and LiOH.H2O (184 mg, 4.38 mmol) were added as a single portion. The reaction mixture was stirred at room temperature for three hours. Solvent was removed under reduced pressure and the remaining aqueous solution was acidified with concentrated HCl to pH˜1. The solution was extracted with EtOAc and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford 1-(5-carboxy-4′-methyl-biphenyl-3-yl)-5-isopropyl-1H-[1,2,3]triazole-4-carboxylic acid light yellow solid (260 mg), which was used without further purification in the next step.

Workup

  1. customSolvent was removed under reduced pressure
  2. extractionThe solution was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f7b39e4034b459d8336e478f8f8ea13
Source dataset
uspto-grants-2011_08
Patent number
US07989637B2

Reaction notes

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