تفاعل #42317

معادلة التفاعل

3-methyl-5-pentanoylbenzoic acid

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

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

HOBt

N-methylmorpholine

EDC

→

title compound

N-{(1R,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-3-methyl-5-pentanoylbenzamide

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, 12/1)

الإجراء التجريبي

To a mixture of 3-methyl-5-pentanoylbenzoic acid (IX-LXXVII, 112 mg, 0.589 mmol), (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol dihydrochloride (VIII, 239 mg, 0.589 mmol), HOBt (80 mg, 0.589 mmol), and N-methylmorpholine (250 mg, 2.47 mmol) in methylene chloride (3 mL) is added EDC (203 mg, 1.06 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, 12/1) gives the title compound, IR (ATR): 3297, 2957, 1687 and 1628 cm−1; APCI-MS (m/z) [M+H]+=539.

المصدر