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

HRID 1056061Notes

Reaction equation

HRID 1056061 reaction equation
C([N:3]([CH2:6]/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])C=O)=O.[C:14]([OH:20])([C:16]([F:19])([F:18])[F:17])=[O:15]>CCO>[F:17][C:16]([F:19])([F:18])[C:14]([OH:20])=[O:15].[NH2:3][CH2:6]/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58465259ethyl (2E)-4-(diformylamino)but-2-enoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

(E)-Ethyl 4-(N-formylformamido)but-2-enoate (3.04 g, 16.43 mmol) was treated with EtOH (20 mL) and TFA (10.0 mL, 130 mmol), fitted with a reflux condenser and heated to 80° C. for 21 h. The mixture was concentrated on the rotovap and dried under high vacuum affording crude (E)-ethyl 4-aminobut-2-enoate 2,2,2-trifluoroacetate as a light yellow viscous liquid: m/z (ESI, +ve ion) 130.1 (M+H)+. The crude material was used in the next step without further purification.

Workup

  1. customfitted with a reflux condenser
  2. concentrationThe mixture was concentrated on the rotovap
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-8ca53ea318c94bb6a226c37171b41682
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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