Reaktion #579247

ord-183cfd088c8d459abe9c8b1ac3aff9ac

Reaktionsgleichung

N[C@H](CO)C(=O)O
D-serine
O=C(OCCOC(=O)c1ccccc1)ON1C(=O)CCC1=O
(2,5-dioxoazolidinyloxycarbonyloxy)ethyl benzoate
→
O=C(N[C@H](CO)C(=O)O)OCCOC(=O)c1ccccc1
title compound ( 28 )
Ausbeute 69.0%
O=C(N[C@H](CO)C(=O)O)OCCOC(=O)c1ccccc1
(2R)-3-Hydroxy-2-[(phenylcarbonyloxyethoxy)carbonylamino]propanoic Acid
Ausbeute 69.0%

Edukte

—
acyloxyalkyl carbamates
N[C@H](CO)C(=O)O
D-serine
O=C(OCCOC(=O)c1ccccc1)ON1C(=O)CCC1=O
(2,5-dioxoazolidinyloxycarbonyloxy)ethyl benzoate

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 benzoate (614 mg, 2.0 mmol) were reacted to provide 410 mg (69% yield) the title compound (28) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=8.00 (m, 2H), 7.55 (m, 1H), 7.40 (m, 2H), 7.01 (m, 1H), 6.59 (br s, 1H), 6.21 (m, 1H), 4.39 (m, 1H), 4.02 (m, 1H), 3.86 (m, 1H), 1.60 (2d, 3H). MS (ESI) m/z 298.10 (M+H)+; 315.11 (M+NH4)+; 320.07 (M+Na)+.

Quelle

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