Trifluoroacetic acid → HCID 44547316, compound

HRID 1512862Notes

Reaction equation

HRID 1512862 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[N:31]([CH3:33])[CH:30]=[C:29]4[CH2:34][CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])[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[N:31]([CH3:33])[CH:30]=[C:29]4[CH2:34][CH2:35][C:36]([OH:38])=[O:37])[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 59146134HCID 59146134, compound

Product 1

HCID 44547316HCID 44547316, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.62 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)-1-methyl-1H-indol-3-yl]propanoate (D8) (80 mg) in dichloromethane (1 mL) at RT. The resulting solution was stirred for 1 hour. The reaction mixture was concentrated. The residue was recrystallized from ether/hexane to afford 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]propanoic acid (E2) (45 mg) as a pale yellow solid. δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 2.65 (2H, q), 2.96 (2H, t), 3.63 (3H, s), 4.89 (1H, m), 7.18 (1H, t), 7.20 (1H, s), 7.45 (2H, m), 7.81 (1H, dd), 8.14 (1H, dd), 8.21 (1H, d), 12.14 (1H, br s). MS (ES): C23H22ClN3O4 requires 439; found 440.0 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-c675ed51cde94da7830804043bac029e
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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