Ethyl 2-amino-3-sulfanylpropanoate → Ethyl 2-Amino-3-(2-furanylthio)propanoate

HRID 568892

Reaktionsgleichung

Reaktionsgleichung von HRID 568892
CO[CH:3]1[CH:7]=[CH:6][CH:5](OC)[O:4]1.[NH2:10][CH:11]([CH2:17][SH:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(#N)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>[NH2:10][CH:11]([CH2:17][S:18][C:5]1[O:4][CH:3]=[CH:7][CH:6]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

5

Edukt 2

HCID 3297Ethyl 2-amino-3-sulfanylpropanoateHCID 789742,5-Dihydro-2,5-dimethoxyfuran

Produkt 1

HCID 20149579Ethyl 2-Amino-3-(2-furanylthio)propanoateAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 73974-Toluenesulfonyl chlorideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To 16.25 g (125 mmol) of 2,5-dimethoxy-2,5-dihydrofuran and 23.20 g (125 mmol) of ethyl 2-amino-3-mercaptopropanoate in 100 ml dry acetonitrile was added approximately 0.15 g of tosyl chloride. The mixture was stirred 1 hour at room temperature under nitrogen during which time complete solution was attained which became very dark. The mixture was concentrated in vacuo, taken up in ethyl acetate, then extracted with aqueous NaHCO3 solution followed by saturated NaCl solution. The organic portion was dried over MgSO4, filtered then concentrated to 50 ml. The concentrate was then chromatographed to give 8.35 g (31.0%) of the title compound as a dark oil.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with aqueous NaHCO3 solution
  3. dry with materialThe organic portion was dried over MgSO4
  4. filtrationfiltered
  5. concentrationthen concentrated to 50 ml
  6. customThe concentrate was then chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-b2d631c393184639b9838869c6e2b4a4
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04730044

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