Reaktion #579244

Reaktionsgleichung

D-serine

(2,5-dioxoazolidinyloxycarbonyloxy)ethyl 2-methylbenzoate

→

title compound ( 25 )

Ausbeute 33.0%

(2R)-3-Hydroxy-2-{[(2-methylphenylcarbonyloxy)ethoxy]carbonylamino}propanoic Acid

Ausbeute 33.0%

Reaktionsbedingungen

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-methylbenzoate (642 mg, 2.0 mmol) were reacted to provide 203 mg (33% yield) of the title compound (25) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=7.85 (br d, 1H), 7.39 (m, 1H), 7.20 (m, 2H), 7.01 (m, 1H), 6.61 (br s, 1H), 6.08 (t, 1H), 4.40 (m, 1H), 4.02 (m, 1H), 3.94 (m, 1H), 2.58 (s, 3H), 1.58 (2d, 3H). MS (ESI) m/z 312.01 (M+H)+; 329.08 (M+NH4)+; 334.06 (M+Na)+.

Quelle