Réaction #89694

Équation de réaction

(2S)-benzylamino-succinic acid 1-benzyl ester 4-tert-butyl ester

K2CO3

NaI

3-chloro-2-chloromethyl-1-propene

→

(2S)-[benzyl-(2-chloromethyl-allyl)-amino]-succinic acid 1-benzyl ester 4-tert-butyl ester

Rendement 58.3%

Solvants

MeCN

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling
2. 2
   Filtrationthe reaction mixture was filtered
3. 3
   Concentrationthe filtrate was concentrated under reduced pressure
4. 4
   AutrePurification by Combiflash (hexane and ethyl acetate: gradient 0 to 8% during 12 min)

Mode opératoire

A mixture of (2S)-benzylamino-succinic acid 1-benzyl ester 4-tert-butyl ester (12.1 g, 32.6 mmol), K2CO3 (14 g, 3 equiv.), NaI (3.0 g, 20 mmol) and 3-chloro-2-chloromethyl-1-propene (5.1 g, 40.8 mmol) in MeCN (150 mL) was stirred at 81° C. for 16 h. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification by Combiflash (hexane and ethyl acetate: gradient 0 to 8% during 12 min) afforded (2S)-[benzyl-(2-chloromethyl-allyl)-amino]-succinic acid 1-benzyl ester 4-tert-butyl ester (8.7 g, 58%). MS (ESI): 458 (M+Na+).

Source