تفاعل #739602

معادلة التفاعل

N-[[5-(Trifluoromethyl)-6-methoxy-1-naphthalenyl]thioxomethyl]-N-methylglycine

1-hydroxybenzotriazole

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

triethylamine

D-Glucosamine hydrochloride

triethylamine

→

2-Deoxy-2-[[[[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]methylamino]acetyl]amino]-D-glucose

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was cooled in ice
2. 2
   workup.STIRRINGThe reaction mixture was stirred at 0° C. for 1 hour
3. 3
   workup.WAITat room temperature over night
4. 4
   أخرىevaporated
5. 5
   أخرىThe residue was triturated with water
6. 6
   ترشيحfiltered
7. 7
   غسيلThe solids were washed with H2O
8. 8
   أخرى1NHCl, 5% NaHCO3, H2O and crystallized from 8/5 H2O/MeOH
9. 9
   أخرىto yield 3.63 g, 67.7%
10. 10
    أخرىThe product was further purified by recrystallization

الإجراء التجريبي

N-[[5-(Trifluoromethyl)-6-methoxy-1-naphthalenyl]thioxomethyl]-N-methylglycine (3.57 g, 0.010 mol), 1-hydroxybenzotriazole (2 g, 0.015 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.3 g, 0.012 mol) and triethylamine (3.5 mol, 0.025 mol) were dissolved in dimethylformamide (25 ml). The mixture was cooled in ice and stirred for 1 hour. D-Glucosamine hydrochloride (2.38 g, 0.011 mol), and additional triethylamine (2.0 mol) were added to the cold reaction mixture. The reaction mixture was stirred at 0° C. for 1 hour, and at room temperature over night and evaporated. The residue was triturated with water and filtered. The solids were washed with H2O, 1NHCl, 5% NaHCO3, H2O and crystallized from 8/5 H2O/MeOH to yield 3.63 g, 67.7%. The product was further purified by recrystallization from boiling methanol (3.1 g), m.p. 166°-169° C. (dec.) as yellow crystals.

المصدر