Trifluoroacetic acid → HCID 22504112, compound

HRID 1814341Notes

Reaction equation

HRID 1814341 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][CH:8]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][CH2:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[O:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])(=[O:14])=[O:13])[CH:9]=[O:10])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:39][N:37]([CH3:38])[CH2:36][CH2:35][O:34][C:25]1[CH:26]=[CH:27][C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:24]=1[CH2:23][CH2:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:12]([NH:11][CH:8]([CH:9]=[O:10])[CH2:7][C:6]([OH:40])=[O:5])(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 865882333-(2-{2-[2-(2-Dimethylamino-ethoxy)-naphthalen-1-yl]-ethoxy}-benzenesulfonylamino)-4-oxo-butyric acid tert-butyl ester

Product 1

HCID 22504112HCID 22504112, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-{2-[2-(2-Dimethylamino-ethoxy)-naphthalen-1-yl]-ethoxy}-benzenesulfonylamino)-4-oxo-butyric acid tert-butyl ester (190 mg, 0.33 mmol) was stirred with trifluoroacetic acid (0.4 mL) in CH2Cl2 (1.2 mL) at room temperature for 1 h. Analytical HPLC analysis indicated the reaction was complete. The reaction mixture was concentrated. Residual trifluoroacetic acid was azeotroped with toluene. The crude product was purified by preparative HPLC to give 3-(2-{2-[2-(2-Dimethylamino-ethoxy)-naphthalen-1-yl]-ethoxy}-benzenesulfonylamino)-4-oxo-butyric acid (31 mg, 0.060 mmol) as a white solid in 18% yield. MS (APCI) m/z 515.1 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customResidual trifluoroacetic acid was azeotroped with toluene
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-b21211b62abc4a268c96d22c70418bbd
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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