Benzyl chloroformate → Ethyl 3-(((benzyloxy)carbonyl)amino)-2,2-dimethylpropanoate

HRID 725649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 725649
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15](=[O:21])[C:16]([CH3:20])([CH3:19])[CH2:17][NH2:18])[CH3:13]>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH2:12]([O:14][C:15](=[O:21])[C:16]([CH3:20])([CH3:19])[CH2:17][NH:18][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH3:13]

Komponenten

5

Edukt 2

HCID 10387Benzyl chloroformateHCID 421529Ethyl 3-amino-2,2-dimethylpropanoate

Produkt 1

HCID 22364460Ethyl 3-(((benzyloxy)carbonyl)amino)-2,2-dimethylpropanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

31 ml of 90% chloroformic acid benzyl ester are slowly added, at 0°-5° C., to 29.04 g of 3-amino-2,2-dimethylpropionic acid ethyl ester in 500 ml of ethyl acetate and 250 ml of 1M sodium hydrogen carbonate solution. The reaction mixture is stirred for 2 hours at 0°-5° C. and extracted with ethyl acetate. The organic phases are washed with saturated sodium chloride solution and then concentrated. The evaporation residue is purified by FC (1 kg of silica gel; eluant: ethyl acetate/hexane=1:3). The title compound is obtained: Rf (ethyl acetate/hexane=1:3)=0.28.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phases are washed with saturated sodium chloride solution
  3. concentrationconcentrated
  4. customThe evaporation residue is purified by FC (1 kg of silica gel; eluant: ethyl acetate/hexane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-bc72e3aec7024d88880ab551dba250c6
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05705658

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