Trifluoroacetic acid → HCID 178436985, compound

HRID 1488155Notes

Reaction equation

[F:1][C:2](F)=[C:3]([CH2:18][CH3:19])[C:4]([C:6]1[C:7]([CH3:17])=[CH:8][C:9]([CH3:16])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12])=O.O.[NH2:22][NH2:23].FC(F)(F)C(O)=O>C1COCC1.O>[CH2:18]([C:3]1[C:2]([F:1])=[N:22][NH:23][C:4]=1[C:6]1[C:7]([CH3:17])=[CH:8][C:9]([CH3:16])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12])[CH3:19]

Participants

Conditions

Temperature: 50 °C

Procedure

Into a 250-mL round-bottom flask, was placed a solution of methyl 5-(2-(difluoromethylene)butanoyl)-2,4-dimethylbenzoate (compound 255.3, 175 mg, 0.62 mmol) in THF (100 mL). At room temperature, hydrazine hydrate (120 μL, 2.48 mmol) was added followed by trifluoroacetic acid (144 μL, 1.88 mmol), then the solution was stirred at 50° C. for 1.5 h. The reaction was cooled to room temperature, carefully diluted with water and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by a silica gel column with ethyl acetate/hexane (1:10) as eluent to obtain the title compound as a yellow oil (90 mg, 53%).

Workup

customInto a 250-mL round-bottom flask, was placed
temperatureThe reaction was cooled to room temperature
extractionthe mixture was extracted with ethyl acetate (3×50 mL)
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by a silica gel column with ethyl acetate/hexane (1:10) as eluent

Sources & evidence

ORD record: ord-28eecef7978f47f3b0a95e21ceefe611
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428502B2

Reaction notes

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