تفاعل #42315

معادلة التفاعل

3-[(dipropylamino)carbonyl]-5-(3-thienyl)benzoic acid

(2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol dihydrochloride

(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol trifluoroacetate

HOBt

triethylamine

EDC

→

title compound

N1-{(1S,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N3,N3-dipropyl-5-(3-thienyl)isophthalamide hydrochloride

المذيبات

DMF

water

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction mixture is stirred for 4 hours
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   غسيلThe organic phase is washed with hydrochloric acid (1 N), water, and saline
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىRecrystallization (methylene chloride/hexanes, 1/1)

الإجراء التجريبي

A mixture of 3-[(dipropylamino)carbonyl]-5-(3-thienyl)benzoic acid (IX-L, step 4, 0.26 g, 0.79 mmol), (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol dihydrochloride (VIII, 0.26 g, 0.71 mmol), HOBt (0.16 g, 1.18 mmol), and triethylamine (0.44 mL, 3.15 mmol) in DMF (4 mL) is stirred at 20-25 degrees C. for 10 minutes EDC (0.23 g, 1.18 mmol) is added and the reaction mixture is stirred for 4 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The organic phase is washed with hydrochloric acid (1 N), water, and saline, dried over magnesium sulfate and concentrated under reduced pressure. Recrystallization (methylene chloride/hexanes, 1/1) gives the title compound, mp=199-201 degrees C.; IR (KBr): 3278, 2961, 2874 and 2837 cm−1; ESI-MS (m/z) [M+H]+=614.

المصدر