Potassium Carbonate → (R)-methyl-3-(5-methoxypyridin-2-ylamino)-2-(oxirane-2-ylmethoxy)benzoate

HRID 912432Notes

Reaction equation

HRID 912432 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][N:12]=2)[C:5]=1[OH:19].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:25][C@@H:26]1[O:28][CH2:27]1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][N:12]=2)[C:5]=1[O:19][CH2:25][C@H:26]1[CH2:27][O:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14292098(R)-(-)-Glycidyl-4-nitrobenzenesulfonateHCID 67410207Methyl-2-hydroxy-3-(5-methoxypyridin-2-ylamino)benzoate

Product 1

HCID 86761414(R)-methyl-3-(5-methoxypyridin-2-ylamino)-2-(oxirane-2-ylmethoxy)benzoateYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl-2-hydroxy-3-(5-methoxypyridin-2-ylamino)benzoate 0.91 g (3.3 mmol) of step 4 in dimethylformamide 10 mL were (R)-glycidyl nosylate 1.0 g (4 mmol) and K2CO3 0.5 g (3.6 mmol), followed by stirring at room temperature for 12 hrs. The reaction mixture was concentrated in a vacuum, diluted with ethylacetate, and washed with distilled water and a saturated NaCl solution. After drying over magnesium sulfate and vacuum concentration, purification by column chromatography (developing solvent: ethylacetate/hexane=1/2) afforded 0.95 g of the title compound (yield 87%).

Workup

  1. concentrationThe reaction mixture was concentrated in a vacuum
  2. additiondiluted with ethylacetate
  3. washwashed with distilled water
  4. dry with materialAfter drying over magnesium sulfate and vacuum concentration, purification by column chromatography (developing solvent: ethylacetate/hexane=1/2)

Sources & evidence

ORD record
ord-49aa13cd709f41898320ef564f6129ec
Source dataset
uspto-grants-2011_09
Patent number
US08026235B1

Reaction notes

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