Acetamide → Methyl 3-(4-(3-chloro-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

HRID 534844Notes

Reaction equation

HRID 534844 reaction equation
[C:1]([O:9][CH2:10][C:11]([C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([Cl:23])[CH:14]=1)=O)(=O)[CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].C([NH2:27])(=O)C.B(F)(F)F.CCOCC>C(OCC)(=O)C>[Cl:23][C:15]1[CH:14]=[C:13]([C:11]2[N:27]=[C:1]([CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5])[O:9][CH:10]=2)[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=1

Participants

5

Reactant 3

HCID 178AcetamideHCID 8000Boron trifluoride etherateHCID 667508792-(3-Chloro-5-(trifluoromethyl)phenyl)-2-oxoethyl methyl succinate

Product 1

HCID 66751004Methyl 3-(4-(3-chloro-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoateYield 39%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 2-(3-chloro-5-(trifluoromethyl)phenyl)-2-oxoethyl methyl succinate (Reference Example 35, 1.10 g, 3.12 mmol), acetamide (0.921 g, 15.59 mmol) and boron trifluoride diethyl etherate (0.565 g, 3.98 mmol) was heated at 140° C. for 2 h. After this time, the reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with saturated sodium bicarbonate, water, and saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate 4:1) to provide methyl 3-(4-(3-chloro-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (0.401 g, 39%) as a yellow viscous oil.

Workup

  1. washwashed with saturated sodium bicarbonate, water, and saturated sodium chloride
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-28c4e68b3f464cdfa1322c561cdc1b40
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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