Methanol → HCID 178494842, compound

HRID 541320Notes

Reaction equation

HRID 541320 reaction equation
[CH:1]([C:4]1[C:13]([C:14]2[NH:18][C:17]([CH2:19][CH2:20][O:21][CH3:22])=[N:16][N:15]=2)=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([CH3:23])[CH:5]=1)([CH3:3])[CH3:2].O.[OH-].[Li+].CO>O>[CH:1]([C:4]1[C:13]([C:14]2[NH:18][C:17]([CH2:19][CH2:20][O:21][CH3:22])=[N:16][N:15]=2)=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:23])[CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 178494843HCID 178494843, compound2×

Product 1

HCID 178494842HCID 178494842, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To crude methyl 4-isopropyl-5-(5-(2-methoxyethyl)-4H-1,2,4-triazol-3-yl)-2-methylbenzoate (compound 198.5, 0.12 mmol, 1.0 equiv) from the previous step in a 4-mL vial was added lithium hydroxide monohydrate (10.1 mg, 0.24 mmol, 2.0 equiv), methanol (0.9 mL) and water (0.3 mL). The resulting mixture was stiffed at room temperature for 3 hours followed by 50° C. for 3 hours and 40° C. for 17 hours. The solvents were removed in vacuo and the residue was diluted with water (7 mL) plus saturated NaHCO3 (1 mL) and the aqueous was washed with diethyl ether (2 mL). The organic was back extracted with a mix of water (2 mL) plus saturated NaHCO3 (0.5 mL). The combined aqueous was acidified to pH=3 with 1 M H3PO4 and extracted with dichlormethane (3×5 mL). The organics were dried (Na2SO4), filtered and removed in vacuo to obtain the title compound as a white waxy solid (31.5 mg, 88% over 2 steps). m/z (ES+) 304 (M+H)+.

Workup

  1. waitfollowed by 50° C. for 3 hours and 40° C. for 17 hours
  2. customThe solvents were removed in vacuo
  3. additionthe residue was diluted with water (7 mL) plus saturated NaHCO3 (1 mL)
  4. washthe aqueous was washed with diethyl ether (2 mL)
  5. extractionThe organic was back extracted with
  6. additiona mix of water (2 mL) plus saturated NaHCO3 (0.5 mL)
  7. extractionextracted with dichlormethane (3×5 mL)
  8. dry with materialThe organics were dried (Na2SO4)
  9. filtrationfiltered
  10. customremoved in vacuo

Sources & evidence

ORD record
ord-9e320149619f45a0bdd96b31b5785d84
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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