Sodium Hydroxide → HCID 10023542, compound

HRID 1532721Notes

Reaction equation

HRID 1532721 reaction equation
[C:1]([CH:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:12][CH:11]=1)[C:5]([O:7]C)=[O:6])(=[O:3])[NH2:2].[OH-].[Na+]>CO.O1CCCC1>[C:1]([CH:4]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:14][CH:15]=1)[C:5]([OH:7])=[O:6])(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10573498HCID 10573498, compound

Product 1

HCID 10023542HCID 10023542, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-carbamoyl-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionate (1.80 g, 4.41 mmol) obtained in Example 2 was dissolved in methanol (20 ml) and tetrahydrofuran (20 ml), and 2.5N aqueous sodium hydroxide solution (2.5 ml, 6.16 mmol) was added at room temperature. The mixture was stirred for 15 hr and the solvent was evaporated. To the residue was added 10% aqueous sodium hydroxide solution (50 ml) and the mixture was washed three times with ethyl acetate (30 ml). To the aqueous layer was added sodium chloride to saturate the same, and the mixture was acidified with 3N hydrochloric acid. The precipitated white solid was collected by filtration, washed with water, and dried to give the title compound (1.70 g, yield 98%).

Workup

  1. customthe solvent was evaporated
  2. additionTo the residue was added 10% aqueous sodium hydroxide solution (50 ml)
  3. washthe mixture was washed three times with ethyl acetate (30 ml)
  4. additionTo the aqueous layer was added sodium chloride
  5. concentrationto saturate the same, and the mixture
  6. filtrationThe precipitated white solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-975e1426e3d041acabc0afc3b3ffcab4
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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