Methanol → HCID 10023542, compound

HRID 1532722Notes

Reaction equation

HRID 1532722 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:29]=[CH:28][C:19]([CH:20]=[C:21]2[C:25](=[O:26])[O:24][NH:23][C:22]2=[O:27])=[CH:18][CH:17]=1.CO>O1CCCC1.[C].[Pd]>[C:22]([CH:21]([CH2:20][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])=[CH:29][CH:28]=1)[C:25]([OH:26])=[O:24])(=[O:27])[NH2:23]

Participants

5

Reactant 2

HCID 887MethanolHCID 54441790HCID 54441790, compound

Product 1

HCID 10023542HCID 10023542, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzilidene]-3,5-isooxazolidinedione (11.5 g, 29.3 mmol) synthesized according to the method described in WO95/18125 was dissolved in tetrahydrofuran (220 ml). 5% Palladium carbon (1.15 g) was added and the mixture was vigorously stirred under a hydrogen atmosphere (normal pressure) at room temperature for 13.5 hr. To the reaction mixture was added methanol (150 ml), and the catalyst was removed by celite filtration. The solvent was evaporated and the residue was suspended in 2.5N aqueous sodium hydroxide solution (50 ml) and washed with ethyl acetate. To the obtained aqueous layer was added 1N hydrochloride (150 ml) and the precipitated white solid was collected by filtration. The solid was washed with water and dried to give the title compound (5.10 g, yield 44%).

Workup

  1. customthe catalyst was removed by celite filtration
  2. customThe solvent was evaporated
  3. washwashed with ethyl acetate
  4. additionTo the obtained aqueous layer was added 1N hydrochloride (150 ml)
  5. filtrationthe precipitated white solid was collected by filtration
  6. washThe solid was washed with water
  7. customdried

Sources & evidence

ORD record
ord-2d081898811a4d9184cb7596d9c96242
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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