Potassium Carbonate → HCID 66917900, compound

HRID 1817998Notes

Reaction equation

HRID 1817998 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH:4]([O:6][C:7]1[C:12]2[N:13](CC3C=CC4C(=CC=CC=4)C=3)[C:14](=[O:17])[CH2:15][O:16][C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:5].BrCC1C=CC2C(=CC=CC=2)C=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:29])[CH:4]([O:6][C:7]1[C:12]2[NH:13][C:14](=[O:17])[CH2:15][O:16][C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 703202-BromomethylnaphthaleneHCID 66917918HCID 66917918, compound

Product 1

HCID 66917900HCID 66917900, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent

Procedure

Synthesis of 2-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yloxy)-propionic acid methyl ester, I-67. A mixture of compound I-66 (350 mg, 1.5 mmol), 2-(bromomethyl) naphthalene (500 mg, 2.25 mmol), KI (374 mg, 2.25 mmol) and K2CO3 (310 mg, 2.25 mmol) in DMF (8 ml) and water (10 drops) was stirred at rt over night and then partitioned between dichloromethane and water. Water layer was extracted with dichloromethane (3×30 ml). The combined organic phase was washed with water (4×30 ml), brine and dried over sodium sulfate. After removal of solvent, the residue was purified by column chromatography on silica gel with EtOAc/hexane as the eluant to give 300 mg of compound I-67. 1H-NMR (500 MHz, CDCl3).

Workup

  1. additionA mixture of compound
  2. custompartitioned between dichloromethane and water
  3. extractionWater layer was extracted with dichloromethane (3×30 ml)
  4. washThe combined organic phase was washed with water (4×30 ml), brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of solvent
  7. customthe residue was purified by column chromatography on silica gel with EtOAc/hexane as the eluant

Sources & evidence

ORD record
ord-0ce88e441a594edb9d627450688f397b
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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