Trifluoroacetic acid → HCID 44547319, compound

HRID 1512866Notes

Reaction equation

HRID 1512866 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]([CH2:34][CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])=[CH:29][N:30]4[CH3:33])=[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]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[CH:29][N:30]4[CH3:33])=[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 59146136HCID 59146136, compound

Product 1

HCID 44547319HCID 44547319, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.878 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)-1-methyl-1H-indol-3-yl]propanoate (D18) (113 mg) in dichloromethane (1.5 mL) at RT. The resulting solution was stirred for 30 min. 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)-1-methyl-1H-indol-3-yl]propanoic acid (E6) (55 mg) as a white solid. MS (ES) C23H22ClN3O4 requires 439; found 440.0 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-8e2e9e2d38624f5ba56d08620bae7a77
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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