Hydrochloric Acid → HCID 17781292, compound

HRID 1532739Notes

Reaction equation

HRID 1532739 reaction equation
[CH3:1][NH:2][C:3]([CH:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:13][CH:12]=1)[C:6]([O:8]C)=[O:7])=[O:4].[OH-].[Na+].Cl.O>CO.O1CCCC1.C(OCC)(=O)C>[CH3:1][NH:2][C:3]([CH:5]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[O:23][C:24]=2[CH3:25])=[CH:15][CH:16]=1)[C:6]([OH:8])=[O:7])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22013855HCID 22013855, compound

Product 1

HCID 17781292HCID 17781292, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 2-methylcarbamoyl-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionate (1.50 g, 3.55 mmol) obtained in Example 31 was dissolved in methanol-tetrahydrofuran (1:1, 40 ml) and 1N aqueous sodium hydroxide solution (20 ml) was added. 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 (100 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 (1.40 g, yield 96%) 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-443de6a95b9f4fdd90154d819af82ac3
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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