Trifluoroacetic acid → 2-(3-Cyclohexyl-6-(methoxycarbonyl)-2-phenyl-1H-indol-1-yl)acetic acid

HRID 505394Notes

Reaction equation

HRID 505394 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=2)[C:10]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[C:9]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.O>[CH:21]1([C:10]2[C:11]3[C:16](=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=3)[N:8]([CH2:7][C:6]([OH:33])=[O:5])[C:9]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66674882methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-phenyl-1H-indole-6-carboxylate

Product 1

HCID 666750062-(3-Cyclohexyl-6-(methoxycarbonyl)-2-phenyl-1H-indol-1-yl)acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

To methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-phenyl-1H-indole-6-carboxylate in DCM/H2O (2:1; 0.15 M), TFA (>300 eq) were added at RT and the reaction left stirring for 1 h. The volatiles were removed in vacuo, and the residue diluted with DCM. The organic phase was washed with brine, dried over Na2SO4, filtered and the solvent evaporated in vacuo to afford the title compound (98%). (ES+) m/z 392 (M+H)+

Workup

  1. waitthe reaction left
  2. customThe volatiles were removed in vacuo
  3. additionthe residue diluted with DCM
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-bc9f2e67503e4c309a22073228f7e33c
Source dataset
uspto-grants-2010_08
Patent number
US07781422B2

Reaction notes

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