Reaktion #3019

Reaktionsgleichung

2,6-dimethoxy-4-methylaniline hydrochloride

N-Boc-glycine

BOP

dimethylformamide

→

N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine

Ausbeute 96.0%

Lösungsmittel

ethyl acetate

triethylamine

diisopropyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe reaction mixture is left at room temperature for 15 hours
2. 2
   Waschenthe organic phase is successively washed with 3×200 ml of water, with a 1N aqueous sodium hydroxide solution
3. 3
   TrocknenThe organic phase is dried over anhydrous sodium sulphate
4. 4
   SonstigeEvaporation of the solvent
5. 5
   Sonstigeleaves a semi-crystalline residue which

Vorschrift

6.6 g of N-Boc-glycine and 15.6 g of BOP are successively added to 100 ml of dimethylformamide and then, at 0° C., 14 ml of triethylamine are added dropwise. The mixture is left for 20 minutes at 0° C. and 6.7 g of 2,6-dimethoxy-4-methylaniline hydrochloride are then added portionwise. The reaction mixture is left at room temperature for 15 hours. 400 ml of ethyl acetate are added to the reaction mixture and the organic phase is successively washed with 3×200 ml of water, with a 1N aqueous sodium hydroxide solution and then with water. The organic phase is dried over anhydrous sodium sulphate. Evaporation of the solvent leaves a semi-crystalline residue which is solidified in diisopropyl ether to provide N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine, in the form of white crystals; M.p.=146° C.; Yield: 96%.

Quelle