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

HRID 541460Notes

Reaction equation

HRID 541460 reaction equation
[CH3:1][C:2]1([CH3:23])[C:10]2[N:9]=[C:8]([C:11]3[C:12]([CH3:22])=[CH:13][C:14]([CH3:21])=[C:15]([CH:20]=3)[C:16]([O:18]C)=[O:17])[NH:7][C:6]=2[CH2:5][O:4][CH2:3]1.[OH-].[Li+]>C1COCC1>[CH3:1][C:2]1([CH3:23])[C:10]2[N:9]=[C:8]([C:11]3[C:12]([CH3:22])=[CH:13][C:14]([CH3:21])=[C:15]([CH:20]=3)[C:16]([OH:18])=[O:17])[NH:7][C:6]=2[CH2:5][O:4][CH2:3]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68288861Methyl 5-(7,7-dimethyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)-2,4-dimethylbenzoate2×

Product 1

HCID 682882695-(7,7-Dimethyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)-2,4-dimethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To methyl 5-(7,7-dimethyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)-2,4-dimethylbenzoate (compound 449.3, 27 mg, 0.086 mmol) in THF (3 mL) was added 2 M lithium hydroxide (430 μl, 0.86 mmol) and the mixture was heated at 50° C. for 16 hrs. The volatile solvents were removed in vacuo and the resulting residue was neutralized with 2M HCl to pH=3 and concentrated in vacuo to give a white solid and used in the next reaction without doing further purification. m/z (ES−) 299 (M−H)−.

Workup

  1. customThe volatile solvents were removed in vacuo
  2. concentrationconcentrated in vacuo
  3. customto give a white solid
  4. customused in the next reaction
  5. custompurification

Sources & evidence

ORD record
ord-50206f6960e04c3f828277d7fb43be2b
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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