Reaktion #52935

Reaktionsgleichung

N-(tert-butoxycarbonyl)-4-(2,6-dichlorobenzyloxy)-3-hydroxy-L-phenylalanine methyl ester

K2CO3

CH3I

→

N-(tert-butoxycarbonyl)-4-(2,6-dichlorobenzyloxy)-3-methoxy-L-phenylalanine methyl ester

Ausbeute 85.5%

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeDMF was removed
2. 2
   Sonstigethe residue was partitioned between water and EtOAc
3. 3
   SonstigeThe organic layer was separated
4. 4
   Extraktionthe aqueous solution was extracted with EtOAc
5. 5
   ExtraktionThe combined extract
6. 6
   Trocknenwas dried (MgSO4)
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe residue was purified by preparative TLC (silica gel; eluent: hexanes/CH2Cl2/EtOAc, 3:3:1)

Vorschrift

To a suspension of N-(tert-butoxycarbonyl)-4-(2,6-dichlorobenzyloxy)-3-hydroxy-L-phenylalanine methyl ester (0.45 g), K2CO3 (0.199 g), and n-Bu4NI (0.035 g) in DME (4.0 mL) was added CH3I (0.072 mL) and the mixture was stirred overnight at room temperature. DMF was removed and the residue was partitioned between water and EtOAc. The organic layer was separated and the aqueous solution was extracted with EtOAc. The combined extract was dried (MgSO4) and evaporated. The residue was purified by preparative TLC (silica gel; eluent: hexanes/CH2Cl2/EtOAc, 3:3:1) to yield 0.396 g of N-(tert-butoxycarbonyl)-4-(2,6-dichlorobenzyloxy)-3-methoxy-L-phenylalanine methyl ester. ESMS: m/z 484 (MH+).

Quelle