Trifluoroacetic acid → 4,4'-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)bis(2-nitroaniline)

HRID 2364788Notes

Reaction equation

HRID 2364788 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:28]=[CH:27][C:16]([NH:17]CC4C=CC(OC)=CC=4)=[C:15]([N+:29]([O-:31])=[O:30])[CH:14]=3)[CH2:11][CH2:10][CH:9]2[C:32]2[CH:47]=[CH:46][C:35]([NH:36]CC3C=CC(OC)=CC=3)=[C:34]([N+:48]([O-:50])=[O:49])[CH:33]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:9]([C:32]3[CH:47]=[CH:46][C:35]([NH2:36])=[C:34]([N+:48]([O-:50])=[O:49])[CH:33]=3)[CH2:10][CH2:11][CH:12]2[C:13]2[CH:28]=[CH:27][C:16]([NH2:17])=[C:15]([N+:29]([O-:31])=[O:30])[CH:14]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866491014,4'-(1-(4-fluorophenyl)pyrrolidine-2,5-diyl)bis(N-(4-methoxybenzyl)-2-nitroaniline)

Product 1

HCID 596167834,4'-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)bis(2-nitroaniline)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 29B (0.78 g, 1.15 mmol) was dissolved in dichloromethane (10 mL) at room temperature and treated with TFA (1.8 mL, 23.0 mmol) for 3 h. The residue was concentrated and partitioned between dichloromethane and sodium bicarbonate solution. The organics were concentrated and purified by chromatography on silica gel with a 40 g column, eluting with dichloromethane to give 0.218 g (43%) of the trans isomer.

Workup

  1. concentrationThe residue was concentrated
  2. custompartitioned between dichloromethane and sodium bicarbonate solution
  3. concentrationThe organics were concentrated
  4. custompurified by chromatography on silica gel with a 40 g column
  5. washeluting with dichloromethane
  6. customto give 0.218 g (43%) of the trans isomer

Sources & evidence

ORD record
ord-20a78689464847499059d1d092b1cdc8
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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