Methanol → 5-(Benzoxazol-2-yl)-1-carboxymethyl-2-methylbenzimidazole

HRID 74275Notes

Reaction equation

HRID 74275 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:27]=[CH:26][C:13]2[N:14]([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1.[OH-].[Na+].CO>C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:27]=[CH:26][C:13]2[N:14]([CH2:18][C:19]([OH:21])=[O:20])[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 674978055-(Benzoxazol-2-yl)-2-methyl-1-tert-butoxycarbonylmethylbenzimidazole

Product 1

HCID 674980835-(Benzoxazol-2-yl)-1-carboxymethyl-2-methylbenzimidazoleYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-(benzoxazol-2-yl)-2-methyl-1-tert-butoxycarbonylmethylbenzimidazole (see Working Example 91-2) (100 mg, 0.275 mmol) in chloroform (3 mL) was added aqueous sodium hydroxide solution (1 M, 0.55 mL, 0.55 mmol). This two-layer solution was homogenized by the addition of methanol, and this was stirred at room temperature for 2 hours. After the reaction was complete, the solution was concentrated, aqueous acetic acid solution was added, and this was stirred at room temperature. The precipitated crystals were filtered, and after washing with water were dried to yield the title compound (76.9 mg, 91% yield) as light yellow crystals.

Workup

  1. concentrationthe solution was concentrated
  2. additionaqueous acetic acid solution was added
  3. stirringthis was stirred at room temperature
  4. filtrationThe precipitated crystals were filtered
  5. washafter washing with water
  6. customwere dried

Sources & evidence

ORD record
ord-c505535102c54ae7a81742dc7d38ba94
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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