Reaction #1121743

Reaction equation

Boc-threonine

glycine ethyl ester hydrochloride

triethylamine

N,N′-dicyclohexylcarbodiimide

hydroxybenzotriazole

→

Boc-Thr-Gly-OEt

Yield 85.4%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherthe mixture was reacted at room temperature for overnight
2. 2
   OtherAfter completion of the reaction, reaction mixture
3. 3
   Filtrationwas filtered
4. 4
   Extractionthe filtrate was extracted with ethyl acetate
5. 5
   ConcentrationThe extract was concentrated under reduced pressure
6. 6
   Otherthe product was crystallized from hexane

Procedure

Boc-threonine (produced by Wako Pure Chemical Industries Ltd.) (11.0 g, 50 mmol) and glycine ethyl ester hydrochloride (produced by Wako Pure Chemical Industries Ltd.) (8.4 g, 60 mmol) were dissolved in dichloromethane (250 mL). After triethylamine (8.4 mL, 60 mmol), N,N′-dicyclohexylcarbodiimide (DCC, 12.4 g, 60 mmol) and hydroxybenzotriazole (9.2 g, 60 mmol) were further added thereto, the mixture was reacted at room temperature for overnight with stirring. After completion of the reaction, reaction mixture was filtered, and then the filtrate was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the product was crystallized from hexane, to obtain Boc-Thr-Gly-OEt (1) (13.0 g) (yield; 85.1%).

Source