Trifluoroacetic acid → 3-[(2,3-Dichlorobenzenesulphonyl)methylamino]propionic acid

HRID 1591744Notes

Reaction equation

HRID 1591744 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([CH2:12][NH:13][CH2:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])(=[O:11])=[O:10].FC(F)(F)C(O)=O>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([CH2:12][NH:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69423846tert.-Butyl 3-[(2,3-dichlorobenzenesulphonyl)methylamino]propionate

Product 1

HCID 694217573-[(2,3-Dichlorobenzenesulphonyl)methylamino]propionic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

For two hours, a solution of 430 mg (1.17 mmol) of tert.-butyl 3-[(2,3-dichlorobenzenesulphonyl)methylamino]propionate and 2.0 ml of trifluoroacetic acid in 30 ml of tetrahydrofuran was stirred at room temperature and then evaporated to dryness. About 30 ml of water were added to the residue and the mixture was extracted three times with in each case 20 ml of ethyl acetate. The organic extracts were washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The product obtained in this manner was reacted further without additional purification.

Workup

  1. customevaporated to dryness
  2. additionAbout 30 ml of water were added to the residue
  3. extractionthe mixture was extracted three times with in each case 20 ml of ethyl acetate
  4. washThe organic extracts were washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness
  7. customThe product obtained in this manner
  8. customwas reacted further without additional purification

Sources & evidence

ORD record
ord-19591513023940aaa5cfa0599bab101d
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

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