Reaktion #579250

ord-4dcd5502f60445369813840a36bac02d

Reaktionsgleichung

N[C@H](CO)C(=O)O
D-serine
CCCCC(=O)OCCOC(=O)ON1C(=O)CCC1=O
(2,5-dioxoazolidinyloxycarbonyloxy)ethyl pentanoate
→
CCCCC(=O)OCCOC(=O)N[C@H](CO)C(=O)O
title compound ( 31 )
Ausbeute 73.0%
CCCCC(=O)OCCOC(=O)N[C@H](CO)C(=O)O
(2R)-3-Hydroxy-2-[(pentanoyloxyethoxy)carbonylamino]propanoic Acid
Ausbeute 73.0%

Edukte

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

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 (504 mg, 4.8 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl pentanoate (1.1 g, 4.0 mmol) were reacted to provide 809 mg (73% yield) of the title compound (31) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.80 (m, 1H), 6.26 (br s, 1H), 5.50 (br s, 1H), 4.40 (m, 1H), 4.02 (m, 1H), 3.85 (m, 1H), 2.36 (m, 2H), 1.60 (m, 2H), 1.47 (d, 3H), 1.37 (m, 2H), 0.91 (t, 3H). MS (ESI) m/z 295.19 (M+NH4)+; 300.08 (M+Na)+; 272.12 (M−H)−.

Quelle

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