Reaktion #86015

ord-0b1b90bbea9a443098457ae8fb781cd2

Reaktionsgleichung

CCOC(=O)CC(NC(=O)OCc1ccccc1)(C(=O)OCC)C(=O)OCC
diethyl 2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinate
→
CCOC(=O)C[C@@](NC(=O)OCc1ccccc1)(C(=O)O)C(=O)OCC
(R)-1-ethyl hydrogen 3-benzyloxycarbonylamino-3-ethoxycarbonylsuccinate
Ausbeute 84.0%

Edukte

CCOC(=O)CC(NC(=O)OCc1ccccc1)(C(=O)OCC)C(=O)OCC
diethyl 2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinate

Reagenzien

Keine

Lösungsmittel

O=P([O-])([O-])[O-]
phosphate
CCO
ethanol

Reaktionsbedingungen

Temperatur
30°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstige4.0 g of pig liver esterase produced by Sigma [PLE (27 kU/g), lyophilized product, product number: E3019]

Vorschrift

4.0 g of pig liver esterase produced by Sigma [PLE (27 kU/g), lyophilized product, product number: E3019] was dissolved in a 0.05 mol/L phosphate buffer adjusted to pH 6.5 (360 mL), and the solution was added with a solution of diethyl 2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinate (4.0 g) dissolved in ethanol (40 mL). The mixture was stirred at 30° C. for 20 hours to obtain (R)-1-ethyl hydrogen 3-benzyloxycarbonylamino-3-ethoxycarbonylsuccinate at a yield of 84% and optical purity of 93.6% ee.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434737B2uspto-grants-2016_09