4-Nitrobenzyl hydrogen malonate

The Uses of 4-Nitrobenzyl hydrogen malonate

4-Nitrobenzyl hydrogen malonate is a reagent used in the synthesis of (±)-thienamycin, a β-Lactam antibiotics. Also, it is useful for chiral key intermediate of carbapenem syntheses.

Preparation

Preparation of mono-4-nitrobenzyl malonate:
In a flame-dried 150 mL pressure tube under argon, add 5.00 g (34.7 mmol) of Meldrum's acid and 40 mL of anhydrous MeCN.
Add 5.58 g (36.4 mmol) of p-nitrobenzyl alcohol to the resulting solution.
Cap the tube tightly and reflux the reaction overnight.
Concentrate the reaction mixture under reduced pressure.
Purify the residue using column chromatography with a 55/45 hexane/EtOAc mixture.
The resulting product is mono-4-nitrobenzyl malonate with a yield of 87%.