HCID 10522854, compound → HCID 10665557, compound

HRID 1532731Notes

Reaction equation

HRID 1532731 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:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26]C)=O)=[CH:18][CH:17]=1.[NH3:28].CO>>[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:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([NH2:28])=[O:26])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 10522854HCID 10522854, compoundHCID 21705897Ammonia methanol

Product 1

HCID 10665557HCID 10665557, compoundYield 80%

Procedure

Methyl 3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionate (600 mg, 1.64 mmol) obtained in Example 16 was added to ammonia/methanol (50 ml), and the mixture was stirred for 24 hr at room temperature. The solvent was evaporated under reduced pressure. Ethyl acetate (50 ml) and 1N aqueous sodium hydroxide solution (50 ml) were added for partition. The organic layer was washed with water (50 ml) and saturated brine (50 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (464 mg, yield 80%) as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionEthyl acetate (50 ml) and 1N aqueous sodium hydroxide solution (50 ml) were added
  3. customfor partition
  4. washThe organic layer was washed with water (50 ml) and saturated brine (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b8e5e5121614ddc96201c0a763fb24d
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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