Trifluoroacetic acid → 2-(4-Bromo-2-fluorobenzyl)-4-(-)-menthyloxycarbonyl-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-acetic acid

HRID 256594Notes

Reaction equation

HRID 256594 reaction equation
C([O:5][C:6](=[O:41])[CH2:7][C:8]1([C:28]([O:30][CH:31]2[CH:36]([CH:37]([CH3:39])[CH3:38])[CH2:35][CH2:34][CH:33]([CH3:40])[CH2:32]2)=[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][CH:31]3[CH:36]([CH:37]([CH3:39])[CH3:38])[CH2:35][CH2:34][CH:33]([CH3:40])[CH2:32]3)=[O:29])([CH2:7][C:6]([OH:41])=[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 677225582-(4-Bromo-2-fluorobenzyl)-4-(-)-menthyloxycarbonyl-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-acetic acid tert-butyl ester

Product 1

HCID 197854242-(4-Bromo-2-fluorobenzyl)-4-(-)-menthyloxycarbonyl-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-bromo-2-fluorobenzyl)-4-(-)-menthyloxycarbonyl-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-acetic acid tert-butyl ester (Diastereomer A) (30.0 g) and trifluoroacetic acid (112.5 g, 76.0 ml) in anhydrous dichloromethane (120 ml) was refluxed for 1.5 hours and concentrated under reduced pressure. The residue was dissolved in a mixture of acetonitrile and toluene. The resulting solution was evaporated under reduced pressure to give the title compound (Diastereomer A) (27.3 g, quantitative) as a brown oil.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in a mixture of acetonitrile and toluene
  4. customThe resulting solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ce6a51d9e8f94ffe82e544306b63d654
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Reaction notes

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