Bromide ion → (S)-2-(4-bromobenzyl)amino-3-methylbutyric acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of 10 g (34.6 mmol) of p-toluenesulphonate of L-valine in 100 mL of CH2Cl2 is added at 20-25° C. and under nitrogen atmosphere 8.0 mL (38 mmol) of 1,1,1,3,3,3-hexamethyldisilazane. After shaking the mixture at 20-25° C. for one hour, 13.2 mL (76 mmol) of diisopropylethylamine and 8.64 g (34.6 mmol) of 4-bromobenzylo bromide are added and heated at reflux. When all the 4-bromobenzylo bromide has been consumed, the solvent is evaporated off at low pressure, 100 mL of water is added and after 1 h at 0° C. the solid is filtered and dried in an air oven at 40° C. to provide 8.8 g (89%) of N-(4-bromobenzyl)-L-valine.

Provenance & Evidence