Reaktion #2041097

Reaktionsgleichung

(S)-2-amino-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester

diisopropylethyl amine

HBTU

FMOC-leucine

DMF

→

title compound

Ausbeute 70.0%

3-(4-Benzyloxy-phenyl)-2-[4-methyl-2-(tetrahydro-pyran-4-ylamino)-pentanoylamino]-propionic acid tert-butyl ester

Ausbeute 70.0%

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting solution was stirred for 30 minutes at 0° C.
2. 2
   Temperaturwarmed to room temperature
3. 3
   Waschenwashed sequentially with IN aqueous HCl, saturated aqueous NaHCO3 (100 mL) and brine (5×100 mL)
4. 4
   SonstigeThe organic phase was collected
5. 5
   Trocknendried over MgSO4
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was triturated with hexane
8. 8
   FiltrationThe product was collected by suction filtration and air
9. 9
   Sonstigedried

Vorschrift

A solution of FMOC-leucine (10.3 g, 29 mmol) in 300 mL of DMF was cooled to 0° C. and treated with diisopropylethyl amine (73 mL) and HBTU (11.1 g, 29.2 mmol). The resulting solution was stirred at 0° C. for 30 minutes and treated with (S)-2-amino-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester (110 g, 36.9 mmol). The resulting solution was stirred for 30 minutes at 0° C. and warmed to room temperature. The reaction mixture was poured into 500 mL of ether and washed sequentially with IN aqueous HCl, saturated aqueous NaHCO3 (100 mL) and brine (5×100 mL). The organic phase was collected, dried over MgSO4 and concentrated to near dryness. The residue was triturated with hexane. The product was collected by suction filtration and air dried to give the title compound as a white solid (12.16 g, 70%); mp 158-160° C.

Quelle