반응 #160681

반응 방정식

N,N′-Dicyclohexyl carbodiimide

pyroglutamic acid

t-butyl dicarbonate

triethylamine

Benzylamine

→

(S)-2-benzylcarbamoyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

수율 17.5%

용매

dimethylformamide

반응 조건

후처리

1. 1
   기타a precipitate formed
2. 2
   workup.ADDITIONwere added
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for 16 h
4. 4
   기타The DMF was removed under vacuum
5. 5
   추출extracted with dichloromethane (DCM; 3×20 ml)
6. 6
   농축The organic layers were concentrated
7. 7
   기타the crude product was purified via silica gel chromatography

실험 절차

N,N′-Dicyclohexyl carbodiimide (DCC; 8.2 g, 40 mmol) was added to a solution of pyroglutamic acid (5.16 g, 40 mmol) in dimethylformamide (DMF; 60 ml). The mixture was stirred at room temperature for 2 h and a precipitate formed. Benzylamine (4.8 ml, 44 mmol) was added and the mixture was stirred for 2 h. t-butyl dicarbonate (Boc2O; 9.6 g, 44 mmol), triethylamine (TEA; 6.3 ml, 44 mmol) and 4-dimethylaminopyridine (DMAP; 488 mg, 4 mmol) were added and the mixture was stirred at room temperature for 16 h. The DMF was removed under vacuum and the residue was taken up with water (20 ml) and extracted with dichloromethane (DCM; 3×20 ml). The organic layers were concentrated and the crude product was purified via silica gel chromatography to afford (S)-2-benzylcarbamoyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (2.23 g, 7.0 mmol, 17.5%).

출처