Ammonia → HCID 22013856, compound

HRID 1532742Notes

Reaction equation

HRID 1532742 reaction equation
[OH:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[C:3](OC)=[O:4].[NH3:29].[OH-].[Na+]>CO.O1CCCC1>[OH:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[C:3]([NH2:29])=[O:4]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 22013861HCID 22013861, compound

Product 1

HCID 22013856HCID 22013856, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 2-hydroxy-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionate (754 mg, 1.98 mmol) obtained in Example 35 was dissolved in methanol-tetrahydrofuran (1:1, 6 ml). 28% Aqueous ammonia (3 ml) was added and the mixture was stirred at room temperature for 2 days. Thereto was added 1N aqueous sodium hydroxide solution (1 ml) and the mixture was stirred for 1 hr. The reaction mixture was partitioned between tetrahydrofuran-ethyl acetate (1:1, 30 ml) and water (10 ml). The organic layer was washed with saturated brine (10 ml), dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (700 mg, yield 96%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. customThe reaction mixture was partitioned between tetrahydrofuran-ethyl acetate (1:1, 30 ml) and water (10 ml)
  3. washThe organic layer was washed with saturated brine (10 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2da57d1d9e654b96ba5be8fbde41b304
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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