Triethylamine → 3-(3-Methoxy-benzenesulfonylamino)-propionic acid ethyl ester

HRID 1060892Notes

Reaction equation

HRID 1060892 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.CCN(CC)CC.Cl.[CH2:21]([O:23][C:24](=[O:28])[CH2:25][CH2:26][NH2:27])[CH3:22]>CC(C)=O>[CH2:21]([O:23][C:24](=[O:28])[CH2:25][CH2:26][NH:27][S:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:11])=[O:10])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27375043-Methoxybenzenesulfonyl chloride

Product 1

HCID 700249813-(3-Methoxy-benzenesulfonylamino)-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

m-Methoxybenzenesulfonyl chloride (3.53 g, 0.017 mol) and Et3N (4.76 mL, 0.034 mol) were dissolved in acetone (35 mL) at 0° C. β-Alanine ethyl ester hydrochloride (2.0 g, 0.017 mol) was added and stirring was continued at room temperature under N2 for 0.5 h. The reaction mixture was concentrated, partitioned between 0.1N HCl solution and EtOAc. The aqueous layer was washed with EtOAc, the organics combined, washed with H2O, brine, and dried (Na2SO4). Filtration and concentration to dryness gave the title compound which was used without further purification.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between 0.1N HCl solution and EtOAc
  4. washThe aqueous layer was washed with EtOAc
  5. washwashed with H2O, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-de8b4f98ef9543a59bc13e92e726d2e5
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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