Trifluoroacetic acid → HCID 22504215, compound

HRID 1814312Notes

Reaction equation

HRID 1814312 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][CH: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[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1)(=[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:13])=[O:14])=[C:16]([O:24][CH2:25][CH2:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)[CH:17]=1)(=[O:23])[NH2:22]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86588214HCID 86588214, compound

Product 1

HCID 22504215HCID 22504215, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[4-carbamoyl-2-(2-naphthalen-1-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester (0.18 g, 0.34 mmol) in dichloromethane (10 mL) and water (0.1 mL) was added trifluoroacetic acid (1 mL). The reaction was stirred for 2 hours at room temperature. The reaction was then concentrated under reduced pressure to yield a colorless oil. The residue was purified by HPLC using a gradient of 10% to 50% acetonitrile containing 0.1% TFA and water at containing 0.1% TFA over 140 minutes to yield 3-[4-carbamoyl-2-(2-naphthalen-1-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid as a lyophilized as a white solid (0.045 g, 28%). MS(APCI) m/z 471.0 (M+1).

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. customto yield a colorless oil
  3. customThe residue was purified by HPLC
  4. additionat containing 0.1% TFA over 140 minutes

Sources & evidence

ORD record
ord-adfa427b58094ffb944dbbecca49339d
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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