Methanol → HCID 178422590, compound

HRID 541324Notes

Reaction equation

HRID 541324 reaction equation
[CH:1]1([C:5]2[C:14]([C:15]3[NH:19][CH:18]=[N: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.CO.O.[OH-].[Li+].OP(O)(O)=O>O>[CH:1]1([C:5]2[C:14]([C:15]3[NH:19][CH:18]=[N: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

6

Reactant 4

HCID 887MethanolHCID 1004Phosphoric AcidHCID 168937Lithium hydroxide, monohydrateHCID 178497404HCID 178497404, compound2×

Product 1

HCID 178422590HCID 178422590, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

To crude methyl 4-cyclobutyl-2-methyl-5-(4H-1,2,4-triazol-3-yl)benzoate (compound 202.2, 0.24 mmol, 1.0 equiv) from the previous step in a 4-mL vial was added methanol (1.5 mL) and water (0.5 mL) and lithium hydroxide monohydrate (20 mg, 0.48 mmol, 2.0 equiv), The resulting mixture was stirred at 40° C. for 42 hours. The reaction mixture was diluted into water (5 mL), acidified to pH 3 with 1M H3PO4 and extracted with DCM (3×5 mL). The organics were dried (Na2SO4), filtered and concentrated in vacuo to obtain the title compound as a white solid (61 mg, 98% over 2 steps). m/z (ES+) 258 (M+H)+.

Workup

  1. extractionextracted with DCM (3×5 mL)
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2b81c40e0c84beea2c1a8fa53119db9
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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