Trifluoroacetic acid → HCID 58641309, compound

HRID 1394930Notes

Reaction equation

HRID 1394930 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])C)=[O:15])[CH:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:10]=1.FC(F)(F)C(O)=O.ClC(OC1C=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40]C=1)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([O:16][C:17]2[CH:20]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:19]=2)=[O:15])[CH:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 821294-Nitrophenyl chloroformateHCID 59001784tert-butyl 4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 58641309HCID 58641309, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flame-dried flask equipped with stir bar under nitrogen was charged 2-3 (0.71 g, 1.98 mmol) and anhydrous CH2Cl2 (50 mL). The resulting solution was treated with trifluoroacetic acid (10 mL) and stirred 1 hour at 25° C. Upon completion, the reaction was concentrated, taken up in CH2Cl2 (50 mL) and washed with 5% NaHCO3 (50 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The resulting free-amine was dissolved in anhydrous CH2Cl2 (50 mL) and treated with p-nitrophenyl chloroformate (0.44 g, 2.17 mmol). The resulting solution was stirred 4 hours at 25° C. until completion. The reaction was concentrated to give 19-1 as a yellow oil: 1H NMR (300 MD, CDCl3) δ 8.22 (d, J=9.4 Hz, 1H), (d, J=9.1 Hz, 1H), 7.38 (m, 5H), 7.02 (m, 5H), 6.43 (m, 1H), 5.85 (m, 1H), 4.90 (m, 2H); LRMS m/z (M+H) 422.9 found, 423.1 required.

Workup

  1. customTo a flame-dried flask equipped
  2. stirringstirred 1 hour at 25° C
  3. concentrationUpon completion, the reaction was concentrated
  4. washwashed with 5% NaHCO3 (50 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe resulting free-amine was dissolved in anhydrous CH2Cl2 (50 mL)
  9. stirringThe resulting solution was stirred 4 hours at 25° C. until completion
  10. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-1b1a5ecf86af4ffda7f48d32987d12b1
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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