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

HRID 47705

Reaktionsgleichung

Reaktionsgleichung von HRID 47705
[C:1]([NH:4][CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].C(=O)([O-])O.[NH4+].O>C(#N)C>[C:1]([NH:4][C@H:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 14013Ammonium BicarbonateHCID 22292739Ethyl 2-(acetylamino)-3-(3-nitrophenyl)propanoate

Produkt 1

HCID 86584419ethyl (2R)-2-(acetylamino)-3-(3-nitrophenyl)propanoateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2.8 g of ethyl 2-(acetylamino)-3-(3-nitrophenyl)propanoate in 17 cm3 of acetonitrile [lacuna] to which is added 3.95 g of ammonium hydrogen carbonate and 35 cm3 of water at a pH in the region of 8. 0.017 g of type-II α-chymotrypsin is then introduced and the mixture is left stirring at room temperature for 1 hour 15 min, while measuring the pH regularly. After this reaction time, the pH is less than 8, a further 0.017 g of type-II α-chymotrypsin is added and stirring of the reaction medium is continued for 2 hours 45 min. The aqueous phase is extracted with 3 times 50 cm3 of ethyl acetate; the combined organic phases are then dried over sodium sulfate, filtered and evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1.4 g of ethyl (2R)-2-(acetylamino)-3-(3-nitrophenyl)propanoate are obtained in the form of white crystals melting at 110° C.

Aufarbeitung

  1. addition0.017 g of type-II α-chymotrypsin is then introduced
  2. waitthe mixture is left
  3. additionAfter this reaction time, the pH is less than 8, a further 0.017 g of type-II α-chymotrypsin is added
  4. stirringstirring of the reaction medium
  5. waitis continued for 2 hours 45 min
  6. extractionThe aqueous phase is extracted with 3 times 50 cm3 of ethyl acetate
  7. dry with materialthe combined organic phases are then dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C

Quellen und Nachweise

ORD-Eintrag
ord-ae19ad4a9f554c3ebcf9eb8e690ab98e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699895B2

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