Sodium Hydroxide → HCID 178494708, compound

HRID 541311Notes

Reaction equation

HRID 541311 reaction equation
[CH:1]1([C:4]2[CH:13]=[C:12]([CH3:14])[C:11]([C:15]3[NH:19][C:18]([CH2:20][O:21][CH3:22])=[N:17][N:16]=3)=[CH:10][C:5]=2[C:6]([O:8]C)=[O:7])[CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[CH:1]1([C:4]2[CH:13]=[C:12]([CH3:14])[C:11]([C:15]3[NH:19][C:18]([CH2:20][O:21][CH3:22])=[N:17][N:16]=3)=[CH:10][C:5]=2[C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178494709HCID 178494709, compound2×

Product 1

HCID 178494708HCID 178494708, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a round-bottom flask was added a solution of methyl 2-cyclopropyl-5-(5-(methoxymethyl)-4H-1,2,4-triazol-3-yl)-4-methylbenzoate (compound 190.7, 200 mg, 0.600 mmol, 1.00 equiv, 90%) in methanol (4 mL). A solution of sodium hydroxide (106 mg, 2.65 mmol, 4.00 equiv) in water (2 mL) was added to the reaction mixture. The resulting solution was stirred for 2 h at 60° C. After cooling to ambient temperature, the organic solvent was removed under reduced pressure and the pH the remaining aqueous layer was adjusted to 2-3 with hydrogen chloride (aq, 6 M). The resulting solids were collected by filtration and dried to yield 170 mg (89%) of the title compound as a white solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe organic solvent was removed under reduced pressure
  3. filtrationThe resulting solids were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-43647e9dede44b40a3b51f0e49d3a562
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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