HCID 68288739, compound → HCID 68289036, compound

HRID 541456Notes

Reaction equation

HRID 541456 reaction equation
[CH:1]1([C:5]2[C:14]([C:15]3[CH:19]=[N:18][NH:17][N:16]=3)=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[C:7]([CH3:20])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1>[OH-].[Na+].CO>[CH:1]1([C:5]2[C:14]([C:15]3[CH:19]=[N:18][NH:17][N:16]=3)=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:20])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 68288739HCID 68288739, compound2×

Product 1

HCID 68289036HCID 68289036, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 4-cyclobutyl-2-methyl-5-(2H-1,2,3-triazol-4-yl)benzoate (compound 446.3, 92 mg, 0.34 M) in 2N NaOH (1.5 ml) and methanol (MeOH) (4 ml) was heated at 50° C. for 16 hours. After cooling to room temperature, the methanol was removed under reduced pressure. The residue was neutralized with 2N HCl to pH 3-4 and extracted with EtOAc. The organic phase was then washed with brine, dried (MgSO4), and concentrated to yield 83 mg of a white solid that was used without further purification. m/z (ES−) 256 (M−H)+.

Workup

  1. customthe methanol was removed under reduced pressure
  2. extractionextracted with EtOAc
  3. washThe organic phase was then washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7c0041ae621f45d1ae47a483bacef07e
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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