Reaktion #579249

ord-f9d4ec5a83ea436b97d0d9fbab19fbf5

Reaktionsgleichung

N[C@H](CO)C(=O)O
D-serine
CCCC(=O)OCCOC(=O)ON1C(=O)CCC1=O
(2,5-dioxoazolidinyloxycarbonyloxy)ethyl butanoate
→
CCCC(=O)OCCOC(=O)N[C@H](CO)C(=O)O
title compound ( 30 )
Ausbeute 48.4%
CCCC(=O)OCCOC(=O)N[C@H](CO)C(=O)O
(2R)-2-[(Butanoyloxyethoxy)carbonylamino]-3-hydroxypropanoic Acid
Ausbeute 48.4%

Edukte

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

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 butanoate (546 mg, 2.0 mmol) were reacted to provide 255 mg (40% yield) the title compound (30) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.80 (m, 1H), 6.09 (t, 1H), 5.81 (br s, 1H), 4.41 (m, 1H), 4.07 (m, 1H), 3.92 (m, 1H), 2.31 (m, 2H), 1.65 (m, 2H), 1.50 (d, 3H), 0.99 (m, 3H). MS (ESI) m/z 286.07 (M+Na)+; 262.06 (M−H)−.

Quelle

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