Trifluoroacetic acid → Trifluoroacetic acid--4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanehydrazide (1/1)

HRID 1968504Notes

Reaction equation

HRID 1968504 reaction equation
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][CH2:10][C:11]([NH:13][NH:14]C(OC(C)(C)C)=O)=[O:12].[C:22]([OH:28])([C:24]([F:27])([F:26])[F:25])=[O:23]>C(Cl)Cl.C(O)C.C1(C)C=CC=CC=1>[F:25][C:24]([F:27])([F:26])[C:22]([OH:28])=[O:23].[O:7]=[C:4]1[CH:5]=[CH:6][C:2](=[O:1])[N:3]1[CH2:8][CH2:9][CH2:10][C:11]([NH:13][NH2:14])=[O:12]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86644087tert-Butyl 2-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoyl)hydrazinecarboxylate

Product 1

HCID 68635864Trifluoroacetic acid--4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanehydrazide (1/1)Yield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21863594Toluene ethanolSolvent

Procedure

To tert-Butyl 2-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoyl)-hydrazinecarboxylate (245) (200 mg, 0.673 mmol) in 8 ml of DCM was added 2 ml of TFA. The mixture was stirred for 45 min, diluted with ethanol/toluene (8 ml, 1:1), evaporated and co-evaporated with ethanol/toluene (3×10 ml), crystallized with ethanol/EtAc/Hexane, filtered, and dried under vaccum to afford 188 mg (90%) of the title compound. 1H NMR (CD3OD) 6.72 (s, 2H), 5.39 (s, 0.6H), 3.47 (t, 2H, J=6.6 Hz), 2.20 (m, 2H), 1.85 (m, 2H); 13C NMR 172.72, 135.56, 54.93, 39.20, 37.99, 25.20; MS m/z+ 197.9 (M+H).

Workup

  1. customevaporated
  2. customcrystallized with ethanol/EtAc/Hexane
  3. filtrationfiltered
  4. customdried under vaccum

Sources & evidence

ORD record
ord-2250e5a18e2a442e86755f62a61c7faf
Source dataset
uspto-grants-2013_04
Patent number
US08426402B2

Reaction notes

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