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

HRID 1060892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060892
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-de8b4f98ef9543a59bc13e92e726d2e5
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525074B2

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