Trifluoroacetic acid → Ethyl 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}butanoate

HRID 561442Notes

Reaction equation

HRID 561442 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11](O)([CH3:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[CH3:27][S:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:38]=1[NH:37][CH:36]=[CH:35]2>ClCCl>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:35]3[C:34]4[C:38](=[C:30]([CH2:29][S:28][CH3:27])[CH:31]=[CH:32][CH:33]=4)[NH:37][CH:36]=3)([CH3:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 55071354Ethyl 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-hydroxybutanoateHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 58392102Ethyl 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}butanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

600 mg (2.25 mmol) of the compound from Example 91A and 0.21 ml (2.70 mmol) of trifluoroacetic acid were added to 399 mg (2.25 mmol) of the compound from Example 8A in 4 ml of dichloromethane. The reaction mixture was stirred at RT for 30 min. Purification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 576 mg (60% of theory) of the title compound.

Workup

  1. customPurification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-01eb02860ee94aeda184a8ee2dc18890
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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