HCID 4327531, compound → HCID 45123189, compound

HRID 490728Notes

Reaction equation

HRID 490728 reaction equation
C[O:2][C:3](=[O:21])[CH:4]([NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[CH:5]([CH3:7])[CH3:6]>C(OC(=O)C)(=O)C>[CH:5]([CH:4]1[C:3](=[O:2])[O:21][C:9]([C:10]2[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=2)=[N:8]1)([CH3:6])[CH3:7]

Participants

3

Reactant 1

HCID 4327531HCID 4327531, compound

Product 1

HCID 45123189HCID 45123189, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
95 °C

Procedure

3-Methyl-2-(4-trifluoromethyl-benzoylamino)-butyric acid methyl ester (4.75 g, 16.42 mmol) is dissolved in acetic anhydride (25 mL) and heated to 95° C. for 3 hr. The mixture is concentrated in vacuo and the residue is partitioned between aqueous saturated sodium hydrogen carbonate (100 mL) and ethyl acetate (100 mL) the layers are separated, the organic phase is washed with water and brine (100 mL each), dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo, and purified over silica gel eluting with 9:1 hexanes:ethyl acetate to afford 4-Isopropyl-2-(4-trifluoromethyl-phenyl)-4H-oxazol-5-one as a colorless oil which solidifies to a white crystalline solid on standing, 4.14 g, 93%. MS (M++1) 272.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe residue is partitioned between aqueous saturated sodium hydrogen carbonate (100 mL) and ethyl acetate (100 mL) the layers
  3. customare separated
  4. washthe organic phase is washed with water and brine (100 mL each)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified over silica gel eluting with 9:1 hexanes

Sources & evidence

ORD record
ord-72372ff2ab52492e8dd990c02f6755a3
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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