Methanol → HCID 59139434, compound

HRID 599855Notes

Reaction equation

HRID 599855 reaction equation
[C:1](=O)([O-])[O-:2].[K+].[K+].[Cl:7][C:8]1[C:9]([O:31][C:32](=[O:36])[N:33]([CH3:35])[CH3:34])=[CH:10][C:11]2[O:16][C:15](=[O:17])[C:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)=[C:13]([CH2:28]Br)[C:12]=2[CH:30]=1.CO.O>C1COCC1>[Cl:7][C:8]1[C:9]([O:31][C:32](=[O:36])[N:33]([CH3:35])[CH3:34])=[CH:10][C:11]2[O:16][C:15](=[O:17])[C:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)=[C:13]([CH2:28][O:2][CH3:1])[C:12]=2[CH:30]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 59139417HCID 59139417, compound

Product 1

HCID 59139434HCID 59139434, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium carbonate (279 mg, 2.01 mmol) was added to a solution of dimethylcarbamic acid 6-chloro-4-bromomethyl-3-(3-nitrobenzyl)-2-oxo-2H-1-benzopyran-7-yl ester (compound 6b-1-3) (500 mg, 1.01 mmol) in THF (7.5 mL)/methanol (5.0 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled away by concentration under reduced pressure, and the resultant residue was purified by column chromatography to yield the title compound (40 mg, 10%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled away by concentration under reduced pressure
  6. customthe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-050309043d1d4b6e8178ea94c6e1857e
Source dataset
uspto-grants-2011_03
Patent number
US07897792B2

Reaction notes

Loading…