Trifluoroacetic acid → HCID 44547315, compound

HRID 1512861Notes

Reaction equation

HRID 1512861 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:25]=[CH:26][CH:27]=[C:28]4[C:32]=3[NH:31][CH:30]=[C:29]4[CH2:33][CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])[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:25]=[CH:26][CH:27]=[C:28]4[C:32]=3[NH:31][CH:30]=[C:29]4[CH2:33][CH2:34][C:35]([OH:37])=[O:36])[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59146101HCID 59146101, compound

Product 1

HCID 44547315HCID 44547315, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.32 mL) was added to a solution of 1,1-dimethylethyl 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (D7) (40 mg) in dichloromethane (0.5 mL) at RT for 1 hour. The reaction mixture was concentrated. The residue was recrystallized from dichloromethane/ether to afford 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid (E1) (30 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 2.65 (2H, q), 3.01 (2H, t), 4.91 (1H, m), 7.22 (1H, t), 7.28 (1H, d), 7.46 (1H, d), 7.83 (1H, d), 7.95 (1H, dd), 8.21 (1H, dd), 8.39 (1H, d), 10.86 (1H, s), 12.12 (1H, br s). MS (ES): C22H20ClN3O4 requires 425; found 425.9 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-ce6eca00d8a948caa14a03de313f0fb2
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

Loading…