Potassium Hydroxide → HCID 59587504, compound

HRID 389759Notes

Reaction equation

HRID 389759 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]([O:23]CC)=[O:22])=[CH:5][CH:4]=1.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][C:12]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]([OH:23])=[O:22])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68521605HCID 68521605, compound

Product 1

HCID 59587504HCID 59587504, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of ethyl 5-(4-methoxyphenyl)-2-(phenylamino)oxazole-4-carboxylate in MeOH (5 mL) at 55° C. was added 1M aqueous potassium hydroxide solution (2.075 mL, 2.08 mmol) and the reaction mixture stirred at 55° C. overnight. The reaction was cooled to room temperature and the MeOH removed in vacuo. The remaining solution was diluted with water and washed with DCM. The aqueous phase was acidified with 2M aqueous HCl (2 mL) and extracted with EtOAc. The combined organic phase was washed with brine, dried over MgSO4 and the solvent removed in vacuo to afford 5-(4-methoxyphenyl)-2-(phenylamino)oxazole-4-carboxylic acid (0.012 g, 0.039 mmol, 48%) as a white solid which was used without further purification. LCMS (1) Rt: 1.44 min; m/z (ES+) 311.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe MeOH removed in vacuo
  3. additionThe remaining solution was diluted with water
  4. washwashed with DCM
  5. extractionextracted with EtOAc
  6. washThe combined organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d2d2e568035c43f487f7bb2cd8b81ff0
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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