Trifluoroacetic acid → HCID 21830860, compound

HRID 1600843Notes

Reaction equation

HRID 1600843 reaction equation
[F:1][C:2]([F:22])([CH2:19][CH:20]=[CH2:21])[C:3]([NH:5][N:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[F:22][C:2]([F:1])([CH2:19][CH:20]=[CH2:21])[C:3]([NH:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21830866HCID 21830866, compound

Product 1

HCID 21830860HCID 21830860, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2,2-difluoropent-4-enamido)-1-(t-butoxycarbonyl)piperazine (Example 16, step b) (5.0 g, 16.4 mmol) in 10 ml dichloromethane was treated with 2 ml trifluoroacetic acid. The reaction was concentrated after 24 hours, basified to pH 9 using 4N sodium hydroxide and extracted into dichloromethane. The organic extracts were dried (MgSO4) and concentrated to give 4-(2,2-difluoropent-4-enamido)piperazine as a yellow oil. δH (250 MHz, CDCl3) 2.83-3.01 (6H, m), 3.59-3.63 (2H, t, J=10 Hz), 3.67-3.71 (2H, t, J=10 Hz), 5.23 (1H, s), 5.27-5.30 (1H, d, J=7.5 Hz), 5.79-5.95 (1H, m).

Workup

  1. concentrationThe reaction was concentrated after 24 hours
  2. extractionextracted into dichloromethane
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f1ee25a7afb0462da7826dbf052c56d0
Source dataset
uspto-grants-1999_11
Patent number
US05977116

Reaction notes

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