Trifluoroacetic acid → HCID 10742872, compound

HRID 256593Notes

Reaction equation

HRID 256593 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][C:8]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:13]2[CH:14]=[CH:15][CH:16]=[C:12]2[C:11](=[O:17])[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][C:20]=2[F:26])[C:9]1=[O:27])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:10]2[C:9](=[O:27])[C:8]([C:28]([O:30][CH2:31][CH3:32])=[O:29])([CH2:7][C:6]([OH:33])=[O:5])[N:13]3[CH:14]=[CH:15][CH:16]=[C:12]3[C:11]2=[O:17])=[C:20]([F:26])[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10625859HCID 10625859, compound

Product 1

HCID 10742872HCID 10742872, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-bromo-2-fluorobenzyl)-4-ethoxycarbonyl-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-acetic acid tert-butyl ester (28.7 g) and trifluoroacetic acid (125.1 g, 84.5 ml) in dichloromethane (100 ml) was refluxed for 3 hours and concentrated under reduced pressure. The residue was chromatographed on silica gel using chloroform as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (21.4 g, 3.6%) as colorless crystals, mp 142°-144° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was chromatographed on silica gel
  4. additionFractions containing the title compound
  5. customevaporated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-b281e73e11d54ff198570a94577b0a55
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Reaction notes

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