Hydrochloric Acid → 3-(3-Methoxy-benzenesulfonylamino)-propionic acid

HRID 1060893Notes

Reaction equation

HRID 1060893 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)(=[O:10])=[O:9])C.[OH-].[Na+].Cl>CCO>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([S:8]([NH:7][CH2:6][CH2:5][C:4]([OH:19])=[O:3])(=[O:10])=[O:9])[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 700249813-(3-Methoxy-benzenesulfonylamino)-propionic acid ethyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(3-Methoxy-benzenesulfonylamino)-propionic acid ethyl ester (5.62 g, 0.0196 mol) was dissolved in EtOH (200 mL), treated with 1N NaOH solution (20.54 mL), and stirred at ambient temperature for 18 h. The reaction was acidified with 1N HCl to pH<5, the EtOH was removed in vacuo, and the residue was partitioned between EtOAc and H2O. The aqueous layer was washed with EtOAc, the organics combined, washed H2O, brine, and dried (Na2SO4). Filtration and concentration in vacuo gave the title compound. 1H NMR (CDCl3) δ 7.37-7.46 (m, 3H), 7.09-7.13 (m, 1H), 5.82 (t, 1H, J=7 Hz), 3.87 (s, 3H), 3.2-3.3 (m, 2H), 2.63 (t, 2H, J=6 Hz).

Workup

  1. customthe EtOH was removed in vacuo
  2. customthe residue was partitioned between EtOAc and H2O
  3. washThe aqueous layer was washed with EtOAc
  4. washwashed H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-84877310b21f405fb35ba5fe385d4ca8
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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