Reacción #87102

Ecuación de reacción

4-Chlorobutanoyl chloride

Boc-L-Dap

hydrochloric acid

→

(S)-2-(tert-butoxycarbonylamino)-3-(4-chlorobutanamido)propanoic acid

Rendimiento 64.4%

Disolventes

dioxane

Na2CO3

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to ambient temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   Extracciónextracted with EtOAc (300 mL×3)
4. 4
   LavadoThe combined organic phases were washed with 1N aqueous hydrochloric acid (300 mL×3) and brine (300 mL×1)
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated

Procedimiento

4-Chlorobutanoyl chloride (12.1 g, 86 mmol) was added to a solution of Boc-L-Dap (16.0 g, 78 mmol) in dioxane (160 mL) and 10% aqueous Na2CO3 (180 mL) at 0° C. dropwise. The reaction mixture was stirred at 0° C. for 1 h and then allowed to warm to ambient temperature and stirred overnight. The mixture was acidified with 1N aqueous hydrochloric acid to pH=3 and extracted with EtOAc (300 mL×3). The combined organic phases were washed with 1N aqueous hydrochloric acid (300 mL×3) and brine (300 mL×1), dried over anhydrous sodium sulfate, and concentrated to afford (S)-2-(tert-butoxycarbonylamino)-3-(4-chlorobutanamido)propanoic acid (15.5 g, 64% yield), which was used directly without further purification.

Fuente