Lithium Hydroxide → 2,4-Dimethyl-5-(6-methyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)benzoic acid

HRID 541476Notes

Reaction equation

HRID 541476 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH2:18][O:19][CH:20]([CH3:22])[CH2:21][C:15]=3[N:14]=2)=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Li+]>CO.O>[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH2:18][O:19][CH:20]([CH3:22])[CH2:21][C:15]=3[N:14]=2)=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68288970Methyl 2,4-dimethyl-5-(6-methyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)benzoate2×

Product 1

HCID 682889362,4-Dimethyl-5-(6-methyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)benzoic acidYield 63.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Into around-bottom flask, was placed a solution of methyl 2,4-dimethyl-5-(6-methyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)benzoate (compound 464.7, 100 mg, 0.330 mmol, 1.00 equiv) in methanol (10 mL). A solution of lithium hydroxide (76 mg, 3.17 mmol, 10.0 equiv) in water (10 mL) was added and the resulting solution was stiffed for 4 h at room temperature. The mixture was concentrated in vacuo and then aqueous HCl was added until the pH was 5-6. The mixture was adjusted to pH 5-6 with aqueous HCl and then the resulting mixture was concentrated in vacuo. MeOH (5 mL) was added to the residue and the solids were removed by filtration. The filtrate was concentrated in vacuo to obtain the title compound as a yellow solid (60 mg, 63%).

Workup

  1. customInto around-bottom flask, was placed
  2. concentrationThe mixture was concentrated in vacuo
  3. additionaqueous HCl was added until the pH was 5-6
  4. concentrationthe resulting mixture was concentrated in vacuo
  5. additionMeOH (5 mL) was added to the residue
  6. customthe solids were removed by filtration
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ef3fc6cfe5c44ce5a864238e4ffca65e
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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