Water → ethyl (2R)-2-(acetylamino)-3-(3-thienyl)propanoate

HRID 47716

Reaktionsgleichung

Reaktionsgleichung von HRID 47716
C(=O)([O-])O.[NH4+].O.[C:7]([NH:10][CH:11]([CH2:17][C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:9])[CH3:8]>C(#N)C>[C:7]([NH:10][C@H:11]([CH2:17][C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:9])[CH3:8]

Komponenten

5

Edukt 3

HCID 962WaterHCID 14013Ammonium BicarbonateHCID 22747902Ethyl 2-acetamido-3-(thiophen-3-yl)propanoate

Produkt 1

HCID 86584423ethyl (2R)-2-(acetylamino)-3-(3-thienyl)propanoateAusbeute 45,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3.95 g of ammonium hydrogen carbonate and 35 cm3 of deionized water are added to a stirred solution, under an inert atmosphere, of 2.41 g of ethyl 2-(acetylamino)-3-(3-thienyl)propanoate in 17 cm3 of acetonitrile. 0.017 g of type-II α-chymotrypsin is added and the pH of the reaction medium is then in the region of 8. This mixture is stirred for 1 hour at room temperature and, after checking that the pH is still at 8, a further 0.017 g of type-II α-chymotrypsin is added. After stirring for 1 hour, with the pH remaining constant, a further 0.017 g of type-II α-chymotrypsin is introduced and stirring of the reaction mixture is continued for 19 hours at room temperature. The acetonitrile is evaporated off under reduced pressure (2 kPa) at a temperature in the region of 33° C. and 25 cm3 of ethyl acetate are then added to the residual aqueous phase. The emulsion obtained is filtered through Celite and the aqueous phase is then extracted with twice 25 cm3 of ethyl acetate. The organic phases are combined, washed with twice 15 cm3 of sodium carbonate solution and then evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C. The solid residue is then dried in an oven under vacuum (10 Pa) at room temperature. 1.1 g of ethyl (2R)-2-(acetylamino)-3-(3-thienyl)propanoate are obtained in the form of a beige-colored solid melting at about 75° C.

Aufarbeitung

  1. addition0.017 g of type-II α-chymotrypsin is added
  2. additiona further 0.017 g of type-II α-chymotrypsin is added
  3. stirringAfter stirring for 1 hour, with the pH
  4. additiona further 0.017 g of type-II α-chymotrypsin is introduced
  5. stirringstirring of the reaction mixture
  6. waitis continued for 19 hours at room temperature
  7. customThe acetonitrile is evaporated off under reduced pressure (2 kPa) at a temperature in the region of 33° C. and 25 cm3 of ethyl acetate
  8. additionare then added to the residual aqueous phase
  9. customThe emulsion obtained
  10. filtrationis filtered through Celite
  11. extractionthe aqueous phase is then extracted with twice 25 cm3 of ethyl acetate
  12. washwashed with twice 15 cm3 of sodium carbonate solution
  13. customevaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C
  14. customThe solid residue is then dried in an oven under vacuum (10 Pa) at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-336d168da36a4264891a3782c0be6f9b
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699895B2

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