Reaktion #579248

ord-c7ff4b0ebc6f4c6684b363a4c3a6b793

Reaktionsgleichung

N[C@H](CO)C(=O)O
D-serine
CC(C)C(=O)OCCOC(=O)ON1C(=O)CCC1=O
(2,5-dioxoazolidinyloxycarbonyloxy)ethyl 2-methylpropanoate
→
CC(C)C(=O)OCCOC(=O)N[C@H](CO)C(=O)O
title compound ( 29 )
Ausbeute 40.3%
CC(C)C(=O)OCCOC(=O)N[C@H](CO)C(=O)O
(2R)-3-Hydroxy-2-{[(2-methylpropanoyloxy)ethoxy]carbonylamino}propanoic Acid
Ausbeute 40.3%

Edukte

—
acyloxyalkyl carbamates
N[C@H](CO)C(=O)O
D-serine
CC(C)C(=O)OCCOC(=O)ON1C(=O)CCC1=O
(2,5-dioxoazolidinyloxycarbonyloxy)ethyl 2-methylpropanoate

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewere reacted

Vorschrift

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (252 mg, 2.4 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl 2-methylpropanoate (546 mg, 2.0 mmol) were reacted to provide 212 mg (40% yield) of the title compound (29) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.79 (m, 1H), 6.03 (t, 0.2H), 5.58 (br s, 1H), 4.41 (m, 1H), 4.05 (m, 1H), 3.94 (m, 1H), 2.57 (m, 1H), 1.48 (2d, 3H), 1.19 (2d, 6H). MS (ESI) m/z 281.11 (M+NH4)+; 286.11 (M+Na)+; 262.12 (M−H)−.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07531572B2uspto-grants-2009_05