Trifluoroacetic acid ethanol → ethyl (2E)-4-aminobut-2-enoate trifluoroacetate

HRID 1943623Notes

Reaction equation

HRID 1943623 reaction equation
C([N:3](C=O)[CH2:4]/[CH:5]=[CH:6]/[C:7]([O:9][CH2:10][CH3:11])=[O:8])=O.[F:14][C:15]([F:20])([F:19])[C:16]([OH:18])=[O:17].C(O)C>>[F:14][C:15]([F:20])([F:19])[C:16]([OH:18])=[O:17].[NH2:3][CH2:4]/[CH:5]=[CH:6]/[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

3

Reactant 2

HCID 19378329Trifluoroacetic acid ethanolHCID 58465259ethyl (2E)-4-(diformylamino)but-2-enoate

Product 1

HCID 72699081ethyl (2E)-4-aminobut-2-enoate trifluoroacetate

Procedure

A solution of ethyl (2E)-4-(diformylamino)but-2-enoate (XV) (0.89 mg, 4.8 mmol) in a mixture trifluoroacetic acid-ethanol (absolute) (2:1, 10 mL) was stirred under reflux overnight (the reaction was followed by LC-MS and stopped when complete conversion was achieved). The solvent was evaporated under vacuum to obtain compound ethyl (2E)-4-aminobut-2-enoate trifluoroacetate (IV) as brown oil (undetermined yield), which was used without further purification in the next step.

Workup

  1. temperatureunder reflux overnight (the reaction
  2. customThe solvent was evaporated under vacuum
  3. customto obtain

Sources & evidence

ORD record
ord-c53ed8279bff4145b331eca797379488
Source dataset
uspto-grants-2013_03
Patent number
US08394802B2

Reaction notes

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