Trifluoroacetic acid → HCID 14739533, compound

HRID 1646956Notes

Reaction equation

HRID 1646956 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([C:22]([CH3:27])([CH3:26])[C:23](O)=[O:24])=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:21]3[C:22]([CH3:27])([CH3:26])[C:23]2=[O:24])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14739563HCID 14739563, compound

Product 1

HCID 14739533HCID 14739533, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (5 mL) to 2-[(4-chlorophenyl)amino-a,a-dimethyl-3-pyridineacetic acid (S) (3.00 g, 0.010 mole) in dichloromethane (40 mL). Stir for 16 hours at room temperature. Rotoevaporate to remove the solvent. Add saturated organic solution with MgSO4, filter, and rotoevaporate. Dissolve the oil in dichloromethane, and chromatograph on silica gel, eluting with dichloromethane. Combine the appropriate fractions, and concentrate under reduced pressure to give a solid. Recrystallize with diethyl ether-isopropyl ether to give the title compound AB as a white solid.

Workup

  1. customto remove the solvent
  2. filtrationAdd saturated organic solution with MgSO4, filter
  3. dissolutionDissolve the oil in dichloromethane
  4. washchromatograph on silica gel, eluting with dichloromethane
  5. concentrationconcentrate under reduced pressure
  6. customto give a solid
  7. customRecrystallize with diethyl ether-isopropyl ether

Sources & evidence

ORD record
ord-016eed51ff0c430284c528d9afb32b64
Source dataset
uspto-grants-1993_01
Patent number
US05182289

Reaction notes

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