Trifluoroacetic acid → 3-[4-Carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid

HRID 1814334Notes

Reaction equation

HRID 1814334 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][C@H:8]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:23])[NH2:22])=[CH:17][C:16]=1[O:24][CH2:25][CH2:26][C:27]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:28]=1[CH:29]=[CH:30][CH:31]=[N:32]2)(=[O:14])=[O:13])[CH:9]=[O:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][CH:8]([CH:9]=[O:10])[CH2:7][C:6]([OH:37])=[O:5])(=[O:14])=[O:13])=[C:16]([O:24][CH2:25][CH2:26][C:27]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:28]=2[CH:29]=[CH:30][CH:31]=[N:32]3)[CH:17]=1)(=[O:23])[NH2:22]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86588229(S)-3-[4-carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester

Product 1

HCID 225040443-[4-Carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acidYield 14.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-[4-carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester (0.08 g, 0.15 mmol) in dichloromethane (10 mL) and water (0.1 ml) was added trifluoroacetic acid (1 mL). The reaction was stirred for 1 h at room temperature. The reaction was then concentrated under reduced pressure to yield a clear oil. The residue was purified by reverse phase high-pressure liquid chromatograph using a gradient of 0% to 30% acetonitrile containing 0.1% TFA and water containing 0.1% TFA over 140 minutes to yield 3-[4-carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid as a white solid (0.01 g, 14%). MS(APCI) m/z 472.1 (M+1)

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. customto yield a clear oil
  3. customThe residue was purified by reverse phase high-pressure liquid chromatograph
  4. customover 140 minutes

Sources & evidence

ORD record
ord-6699af3bdef64c6e891139760850a952
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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