Reaction #640584

Reaction equation

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

2-Nitrobenzyl amine hydrochloride

3-hydroxy-3-phenyl propionic acid

triethylamine

hydrochloric acid water

→

3-hydroxy-N-(2-nitrobenzyl)-3-phenyl propionic acid amide

Yield 92.1%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturecooled
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashThe organic layer was washed with a saturated brine
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   Otherthe solvent was evaporated under reduced pressure
6. 6
   OtherThe obtained crude crystal
7. 7
   Washwas washed with a mixture of hexane-ether (2:1)

Procedure

2-Nitrobenzyl amine hydrochloride (2.27 g, 12.0 mmol), 3-hydroxy-3-phenyl propionic acid (2.00 g, 12.0 mmol), triethylamine (1.34 g, 13.3 mmol) were added to tetrahydrofuran (50 ml) and the reaction mixture was ice cooled. Under ice cooled condition, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (3.33 g, 12.0 mmol) was added thereto and stirred at room temperature for five hours. The reaction mixture was poured into dilute hydrochloric acid water and extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude crystal was washed with a mixture of hexane-ether (2:1) to obtain 3-hydroxy-N-(2-nitrobenzyl)-3-phenyl propionic acid amide (3.32 g).

Source