Reacción #1596965

Ecuación de reacción

L-Glu(OBn)-OtBu hydrochloride

triphosgene

L-Lys(Z)-OtBu

triethylamine

→

(9S,13S)-15-benzyl 13,9-di-tert-butyl 3,11-dioxo-1-phenyl-2-oxa-4,10,12-triazapentadecane-9,13,15-tricarboxylate

Disolventes

DCE

DCE

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITto come to room temperature over a period of 1 h
2. 2
   workup.STIRRINGstirred at room temperature overnight
3. 3
   OtroThe reaction was quenched with 1N HCl
4. 4
   Extracciónextracted with DCM
5. 5
   OtroThe organic layer was dried
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   Otrothe residue was purified

Procedimiento

To a solution of L-Glu(OBn)-OtBu hydrochloride (3.13 mg, 9.49 mmol) and triphosgene (923 mg, 3.13 mmol) in DCE (70 mL) cooled to −78° C. was added triethylamine (2.80 mL) under nitrogen. After stirring at −78° C. for 2 h, a solution of L-Lys(Z)-OtBu (3.88 g, 10.40 mmol) and TEA (1.5 mL) in DCE (10 mL) was added. The mixture was allowed to come to room temperature over a period of 1 h and stirred at room temperature overnight. The reaction was quenched with 1N HCl, and extracted with DCM. The organic layer was dried and concentrated under reduced pressure and the residue was purified utilizing a Biotage SP4 to afford (9S,13S)-15-benzyl 13,9-di-tert-butyl 3,11-dioxo-1-phenyl-2-oxa-4,10,12-triazapentadecane-9,13,15-tricarboxylate as a colorless oil (4.71 g, 76%). 1H NMR (400 MHz, CDCl3) δ 7.34-7.29 (m, 10H), 5.13-5.04 (m, 6H), 4.97 (brs, 1H), 4.38-4.28 (m, 2H), 3.18-3.14 (m, 2H), 2.50-2.35 (m, 2H), 2.19-2.10 (m, 1H), 1.94-1.85 (m, 1H), 1.79-1.72 (m, 1H), 1.58-1.33 (m, 21H).

Fuente