Reaktion #579245

ord-4944ed715e24474f92e1349b3f856d24

Reaktionsgleichung

N[C@H](CO)C(=O)O
D-serine
CC(C)CC(=O)OCCOC(=O)ON1C(=O)CCC1=O
(2,5-dioxoazolidinyloxycarbonyloxy)ethyl 3-methylbutanoate
→
CC(C)CC(=O)OCCOC(=O)N[C@H](CO)C(=O)O
title compound ( 26 )
Ausbeute 59.0%
CC(C)CC(=O)OCCOC(=O)N[C@H](CO)C(=O)O
(2R)-3-Hydroxy-2-{[(3-methylbutanoyloxy)ethoxy]carbonylamino}propanoic Acid
Ausbeute 59.0%

Edukte

—
acyloxyalkyl carbamates
N[C@H](CO)C(=O)O
D-serine
CC(C)CC(=O)OCCOC(=O)ON1C(=O)CCC1=O
(2,5-dioxoazolidinyloxycarbonyloxy)ethyl 3-methylbutanoate

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 3-methylbutanoate (574 mg, 2.0 mmol) were reacted to provide 326 mg (59% yield) of the title compound (26) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.80 (m, 1H), 6.11 (m, 1H), 5.78 (br s, 1H), 4.41 (m, 1H), 4.04 (m, 1H), 3.94 (m, 1H), 2.01-2.24 (m, 3H), 1.48 (2d, 3H), 0.99 (2d, 6H). MS (ESI) m/z 278.04 (M+H)+; 295.09 (M+NH4)+; 300.04 (M+Na)+; 276.10 (M−H)−.

Quelle

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