Reaktion #353200

Reaktionsgleichung

t-butyl 2-bromo-3-[(4-nitrophenyl)methoxy]propanoate

diethylenetriamine

→

desired product

Ausbeute 80.0%

N-[2-[(2-aminoethyl)amino]ethyl]-O-(4-nitrophenyl)methyl-D,L-serine t-butyl ester

Ausbeute 80.0%

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigekept at 0°-5° C. and under inert atmosphere
2. 2
   SonstigeThe solvent was evaporated under vacuum and 100 ml of a NaCl saturated solution
3. 3
   workup.ADDITIONwere added to the residue
4. 4
   ExtraktionThe solution was extracted with Et2O
5. 5
   Waschenthe organic phase was washed with H2O
6. 6
   Sonstigedried
7. 7
   Einengenconcentrated under vacuum

Vorschrift

A solution of 14 g of t-butyl 2-bromo-3-[(4-nitrophenyl)methoxy]propanoate (prepared according to the procedure described by P. L. Rings et al., Synth. Commun., 1993, 23, 2639) (0.0389 mol), in 30 ml of acetonitrile was added to a solution of 20 g of diethylenetriamine (0.19 mol) in 20 ml of acetonitrile kept at 0°-5° C. and under inert atmosphere. The solution was then heated to 35° C. for 4 h. The solvent was evaporated under vacuum and 100 ml of a NaCl saturated solution were added to the residue. The solution was extracted with Et2O; the organic phase was washed with H2O, dried and concentrated under vacuum to obtain 12 g of the desired product (0.031 mol).

Quelle