Water → HCID 57770868, compound

HRID 2092630Notes

Reaction equation

HRID 2092630 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-fa9ffcbb41294c42b3b80ee75cce7320
Source dataset
uspto-grants-2013_05
Patent number
US08440708B2

Reaction notes

Loading…