Reacción #64795

Ecuación de reacción

Bis (trimethylsilyl)trifluoroacetamide

(αS)-amino-3-cyanopropanoic acid

Benzylchloroformate

→

(2S)-[[(Phenylmethoxy)carbonyl]amino]-3cyanopropanoic acid

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture was stirred overnight
2. 2
   Concentraciónconcentrated in vacuo
3. 3
   workup.DISSOLUTIONdissolved in ethyl acetate (200 mL)
4. 4
   LavadoThe organic solution was washed with water (2 x) and brine
5. 5
   Secadodried (Na2SO4)
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroCrystallization from isopropyl ether
8. 8
   Otroyielded 3.82 g

Procedimiento

Bis (trimethylsilyl)trifluoroacetamide (9.4 mL, 35 mmol.) was added to a suspension of (αS)-amino-3-cyanopropanoic acid (2.0 g., 17.5 mmol.) in 10 mL of dry acetonitrile and the reaction mixture was stirred for 3 hours. Benzylchloroformate (2.5 mL, 17.5 mmol) was added, the reaction mixture was stirred overnight, concentrated in vacuo, and dissolved in ethyl acetate (200 mL). The organic solution was washed with water (2 x) and brine, dried (Na2SO4), and concentrated in vacuo. Crystallization from isopropyl ether yielded 3.82 g. of the title A product.

Fuente