تفاعل #42326

معادلة التفاعل

(2R,3S)-3-amino-1-{[3-(2,4-dimethylphenyl)propyl]amino}-4-phenyl-2-butanol hydrochloride

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

3-[(dipropylamino)carbonyl]-5-methylbenzoic acid

3-{[[4-(benzyloxy)butyl](propyl)-amino]carbonyl}-5-methylbenzoic acid

HOBt

N-methylmorpholine

EDC

→

title compound

N1-((1S,2R)-1-benzyl-3-{[3-(2,4-dimethylphenyl)propyl]amino}-2-hydroxypropyl)-5-methyl-N3,N3-dipropylisophthalamide

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىpartitioned between ethyl acetate and water
2. 2
   غسيلThe organic phase is washed with hydrochloric acid (1 N), saturated sodium bicarbonate, saline
3. 3
   تجفيفdried (sodium sulfate)
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىPurification by flash column chromatography (silica; methylene chloride/methanol/ammonium hydroxide, 95/5/1)

الإجراء التجريبي

To a stirred mixture of (2R,3S)-3-amino-1-{[3-(2,4-dimethylphenyl)propyl]amino}-4-phenyl-2-butanol hydrochloride (VIII, 163 mg, 0.411 mmol), 3-[(dipropylamino)carbonyl]-5-methylbenzoic acid (IX, 108 mg, 0.411 mmol), HOBt (55 mg, 0.411 mmol), and N-methylmorpholine (133 mg, 1.32 mmol) in methylene chloride (5 mL) is added EDC (142 mg, 0.740 mmol). The reaction mixture is stirred overnight and then partitioned between ethyl acetate and water. The organic phase is washed with hydrochloric acid (1 N), saturated sodium bicarbonate, saline, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica; methylene chloride/methanol/ammonium hydroxide, 95/5/1) gives the title compound, IR (ATR): 3299, 2930 and 1614 cm−1; APCI-MS (m/z) [M+H]+=572.

المصدر