Trifluoroacetic acid → HCID 67083717, compound

HRID 2239512Notes

Reaction equation

HRID 2239512 reaction equation
C(O)(C(F)(F)F)=O.[Na].[CH3:9][O:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:13](/[N:27]=[N:28]/N2CCCC2)[CH:12]=1>>[CH3:18][O:17][C:16]1[CH:15]=[C:14]2[C:13](=[CH:12][C:11]=1[O:10][CH3:9])[NH:27][N:28]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19]2=[O:26]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178472188HCID 178472188, compound

Product 1

HCID 67083717HCID 67083717, compoundYield 51.4%

Conditions

Temperature
0 °C

Procedure

To a 100 mL round bottom flask charged with a magnetic stir bar was added TFA (30 mL). The flask was cooled to 0° C. in an ice bath and ethyl 3-{4,5-dimethoxy-2-[(E)-pyrrolidin-1-yldiazenyl]phenyl}-3-oxopropanoate sodium salt (4.03 g, 10.83 mmol) (Method 3) was added to the reaction mixture in portions over 10 minutes. The mixture was stirred at this temperature for an additional 2 h before being poured over 0° C. ice-water (˜300 mL). The desired product precipitated from the mixture and was collected via vacuum filtration using a Buchner funnel. The solid was rinsed with water (1×100 mL) and diethyl ether (1×100 mL) to yield 1.55 g (51%) of the title compound as an off white solid that was used without further purification. 1H NMR: 13.70 (s, NH, 1H), 7.39 (s, 1H), 7.00 (s, 1H), 4.30 (q, 2H), 3.95 (s, 3H), 3.89 (s, 3H), 1.30 (t, 3H); m/z 279.

Workup

  1. additionTo a 100 mL round bottom flask charged with a magnetic stir bar
  2. customThe desired product precipitated from the mixture
  3. filtrationwas collected via vacuum filtration
  4. washThe solid was rinsed with water (1×100 mL) and diethyl ether (1×100 mL)

Sources & evidence

ORD record
ord-474c9e3b51fc4f53ab9cc3a0ae989e1e
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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