Reaction #8625

Reaction equation

water

Imidazole

homoserine

tert-Butyldimethylsilyl chloride

→

2-amino-4-(tert-butyldimethylsilanyloxy)butyric acid

Solvents

DMF

Conditions

Workup

1. 1
   workup.ADDITIONadded
2. 2
   workup.STIRRINGthe mixture is stirred for ten minutes at 0° C. the for 4 hours at room temperature
3. 3
   Filtrationthe resulting solid is collected by filtration
4. 4
   OtherThe isolated product is dried
5. 5
   Otherused without further purification

Procedure

Imidazole (20.4 g, 300 mmol) is added to a solution of homoserine (11.9 g, 100 mmol) in DMF (100 mL) and the solution is stirred 15 minutes then cooled to 0° C. tert-Butyldimethylsilyl chloride (13.7 g, 91 mmol) added and the mixture is stirred for ten minutes at 0° C. the for 4 hours at room temperature. The reaction mixture is poured into water (3 L) and the resulting solid is collected by filtration. The isolated product is dried and used without further purification.

Source