Trifluoroacetic acid → HCID 44547318, compound

HRID 1512865Notes

Reaction equation

HRID 1512865 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:32]=[C:31]4[C:27]([C:28]([CH2:33][CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])=[CH:29][NH:30]4)=[CH:26][CH:25]=3)[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17]>ClCCl>[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:32]=[C:31]4[C:27]([C:28]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[CH:29][NH:30]4)=[CH:26][CH:25]=3)[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59146052HCID 59146052, compound

Product 1

HCID 44547318HCID 44547318, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.20 mL) was added to a solution of 1,1-dimethylethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (D17) (150 mg) in dichloromethane (2 mL) at RT. The resulting solution was stirred for 1 hour. The reaction mixture was concentrated. The residue was recrystallized from dichloromethane/ether to afford 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid (E5) (105 mg) as a pale pink solid. δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 2.64 (2H, t), 2.97 (2H, t), 4.89 (1H, m), 7.35 (1H, m), 7.45 (1H, d), 7.73 (2H, dd), 8.13 (2H, m), 8.34 (1H, s), 11.22 (1H, s), 12.13 (1H, br s). MS (ES): C22H20ClN3O4 requires 425; found 426.0 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was recrystallized from dichloromethane/ether

Sources & evidence

ORD record
ord-5c0a450914c14626a82938182247a528
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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