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

HRID 421970Notes

Reaction equation

HRID 421970 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-oxo ethyl)-3-cyclo hexyl-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-b3c03a1636c94e028a9ed8249885b5ba
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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