Trifluoroacetic acid → Ethyl 3-(4-chlorophenyl)-2-methyl-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

HRID 561394Notes

Reaction equation

HRID 561394 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[N:18](C(OC(C)(C)C)=O)[CH:17]=2)[CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58392107tert-Butyl 3-[1-(4-chlorophenyl)-3-ethoxy-2-methyl-3-oxopropyl]-7-[(methylsulfanyl)methyl]-1H-indole-1-carboxylate

Product 1

HCID 58392240Ethyl 3-(4-chlorophenyl)-2-methyl-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.85 g (1.69 mmol) of the compound from Example 31A was dissolved in 10 ml of dichloromethane, and 2.61 ml (33.86 mmol) of trifluoroacetic acid were added. After stirring at RT for 2 h, the reaction solution was concentrated and the residue was purified twice by preparative HPLC (mobile phase: acetonitrile-water gradient). 0.42 g (61% of theory) of the title compound was obtained as mixture of diasteromers.

Workup

  1. concentrationthe reaction solution was concentrated
  2. customthe residue was purified twice by preparative HPLC (mobile phase: acetonitrile-water gradient)

Sources & evidence

ORD record
ord-9b53e6c12def45309548f9a21d4d8178
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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