Sulfuric Acid → (2S)-3-benzylthio-2-maleimidopropionic acid

HRID 485270

Reaktionsgleichung

Reaktionsgleichung von HRID 485270
COC(N1[C:9](=[O:10])[CH:8]=[CH:7][C:6]1=[O:11])=O.[CH2:12]([S:19][CH2:20][C@@H:21]([C:23]([OH:25])=[O:24])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+].S(=O)(=O)(O)O>O.C1COCC1.C(Cl)(Cl)Cl.C(OCC)(=O)C.C(O)(=O)C>[CH2:12]([S:19][CH2:20][C@@H:21]([N:22]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]1=[O:11])[C:23]([OH:25])=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 193613S-benzyl-L-cysteineHCID 516892Sodium BicarbonateHCID 580610N-(Methoxycarbonyl)maleimide

Produkt 1

HCID 13490347(2S)-3-benzylthio-2-maleimidopropionic acidAusbeute 19,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 87343015Chloroform ethyl acetate acetic acidLösungsmittel2×

Versuchsvorschrift

According to the method of O. Keller and J. Rudinger (Helv. Chim. Acta., 58, 531 (1975)), 6.2 g (40 mmols) of N-methoxycarbonylmaleimide was added at 0° C. to a solution of 8.44 g (40 mmols)of S-benzyl-L-cysteine in a mixture of 200 ml of saturated aqueous solution of sodium hydrogen carbonate and 100 ml of THF. The mixture was stirred for 10 minutes and then diluted with 300 ml of water and 150 ml of THF. The reaction mixture was stirred at room temperature for 30 minutes and subsequently at 40° C. for 30 minutes, neutralized with concentrated sulfuric acid and thereafter concentrated to about 200 ml in a vacuum. The concentrate was subjected to extraction with ethyl acetate, and the extract was dried over anhydrous sodium sulfate (Na2SO4) and concentrated to give a white solid. The product was subjected to silica gel chromatography (90:10:5 chloroform-ethyl acetate-acetic acid to 40:60:5 chloroform-ethyl acetate-acetic acid), giving 2.29 g of (2S)-3-benzylthio-2-maleimidopropionic acid. M.p.: 86°-87° C.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes and subsequently at 40° C. for 30 minutes
  2. concentrationconcentrated to about 200 ml in a vacuum
  3. extractionThe concentrate was subjected to extraction with ethyl acetate
  4. dry with materialthe extract was dried over anhydrous sodium sulfate (Na2SO4)
  5. concentrationconcentrated
  6. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-4796f2babb304a589c11dfce2f572d94
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04536391

Verknüpfte Notizen

Wird geladen…