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

HRID 874919Notes

Reaction equation

HRID 874919 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-48f87ce256fd4089aa33cc6700a88f3b
Source dataset
uspto-grants-2015_03
Patent number
US08981092B2

Reaction notes

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