3-(3-Methoxy-benzenesulfonylamino)-propionic acid → N-(3-hydroxy-propyl)-3-methoxy-benzenesulfonamide

HRID 1060894Notes

Reaction equation

HRID 1060894 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH2:13][CH2:14][C:15](O)=[O:16])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1>C1COCC1>[OH:16][CH2:15][CH2:14][CH2:13][NH:12][S:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:11])=[O:10]

Participants

3

Reactant 1

HCID 186294403-(3-Methoxy-benzenesulfonylamino)-propionic acid

Product 1

HCID 18629442N-(3-hydroxy-propyl)-3-methoxy-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(3-Methoxy-benzenesulfonylamino)-propionic acid (0.755 g, 2.91 mmol), was dissolved in THF (10 mL), cooled in an ice-H2O bath, and treated with borane THF complex (3.49 mL of a 1M solution, 3.49 mmol) with stirring. After warming to room temperature over 1 h, the reaction was cooled in an ice bath, and quenched by dropwise addition of H2O, then partitioned between H2O and CH2Cl2. The aqueous layer was washed with CH2Cl2 (3×20 mL), dried (MgSO4). Filtration and concentration in vacuo gave the title compound which was used without further purification.

Workup

  1. temperaturecooled in an ice-H2O bath
  2. temperaturethe reaction was cooled in an ice bath
  3. customquenched by dropwise addition of H2O
  4. custompartitioned between H2O and CH2Cl2
  5. washThe aqueous layer was washed with CH2Cl2 (3×20 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-a79f9991b4fe44e892010678ab2e9673
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

Loading…