Dimethyl itaconate → 3-(3-Cyclopentyloxy-4-methoxy-phenyl)-5-methoxy carbonylmethyl-4,5-dihydro-isoxazol-5-carboxylic Acid Methyl Ester

HRID 1169848Notes

Reaction equation

HRID 1169848 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH:10]=[N:11][OH:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][O:19][C:20](=[O:28])[C:21]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH2:22].Cl[O-].[Na+]>O1CCCC1.O>[CH3:18][O:19][C:20]([C:21]1([CH2:23][C:24]([O:26][CH3:27])=[O:25])[O:12][N:11]=[C:10]([C:9]2[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)[CH2:22]1)=[O:28]

Participants

6

Reactant 3

HCID 69240Dimethyl itaconateHCID 28228453-Cyclopentyloxy-4-methoxybenzaldehyde oximeHCID 23665760Sodium Hypochlorite

Product 1

HCID 686864923-(3-Cyclopentyloxy-4-methoxy-phenyl)-5-methoxy carbonylmethyl-4,5-dihydro-isoxazol-5-carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the compound obtained from step b above (1 eq) in tetrahydrofuran, was added dimethylitaconate (2 eq). The reaction mixture was stirred at 60° C. for 0.5 hours followed by the addition of sodium hypochlorite solution. The resulting reaction mixture was stirred at 60-70° C. for 5-6 hours. Tetrahydrofuran was removed under reduced pressure. The residue thus obtained was diluted with water, extracted with ethyl acetate, washed with saturated sodium chloride solution and water. The reaction mixture was dried over anhydrous sodium sulphate and concentrated under reduced pressure to furnish the title compound.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at 60-70° C. for 5-6 hours
  3. customTetrahydrofuran was removed under reduced pressure
  4. customThe residue thus obtained
  5. extractionextracted with ethyl acetate
  6. washwashed with saturated sodium chloride solution and water
  7. dry with materialThe reaction mixture was dried over anhydrous sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-abeda97ba5974419b8d98a14fff7b526
Source dataset
uspto-grants-2010_11
Patent number
US07825147B2

Reaction notes

Loading…