Hydrochloric Acid → HCID 17781266, compound

HRID 1532736Notes

Reaction equation

HRID 1532736 reaction equation
[C:1]([C:4]([CH3:31])([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+].Cl.O>CO.O1CCCC1.C(OCC)(=O)C>[C:1]([C:4]([CH3:31])([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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22013862HCID 22013862, compound

Product 1

HCID 17781266HCID 17781266, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 2-carbamoyl-2-methyl-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionate (1.17 g, 2.77 mmol) obtained in Example 27 was dissolved in methanol-tetrahydrofuran (1:1, 20 ml). 1N Aqueous sodium hydroxide solution (10 ml) was added and the mixture was stirred at room temperature for 1 hr. 1N Hydrochloric acid was added to acidify the reaction mixture, and water (50 ml) and ethyl acetate (150 ml) were added for partition. The organic layer was washed with saturated brine (50 ml), dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (1.02 g, yield 90%) as a white solid.

Workup

  1. additionwere added
  2. customfor partition
  3. washThe organic layer was washed with saturated brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1e48d848f124a59995d6a8ee378a5d5
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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