Reaktion #42311

Reaktionsgleichung

5-[(dipropylamino)carbonyl][1,1′-biphenyl]-3-carboxylic 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

N3-{(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N5,N5-dipropyl[1,1′-biphenyl]-3,5-dicarboxamide hydrochloride

Lösungsmittel

methylene chloride

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture is stirred at 20-25 degrees C
2. 2
   Sonstigeovernight
3. 3
   WaschenThe reaction mixture is washed with water, 1 N hydrochloric acid, water, and saline
4. 4
   Trocknendried (sodium sulfate)
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

A mixture of 5-[(dipropylamino)carbonyl][1,1′-biphenyl]-3-carboxylic acid (IX, 188 mg, 0.56 mmol), (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol dihydrochloride (VIII, Step 2, 230 mg, 0.56 mmol), HOBt (114 mg, 0.84 mmol), and N-methylmorpholine (0.23 g, 2.24 mmol) in methylene chloride (6 mL) and dimethylformamide (1 mL) is stirred at 20-25 degrees C. for 15 minutes EDC (161 mg, 0.84 mmol) is added and the reaction mixture is stirred at 20-25 degrees C. overnight. The reaction mixture is washed with water, 1 N hydrochloric acid, water, and saline, dried (sodium sulfate), and concentrated under reduced pressure to give the title compound, mp 230-233degrees C.; IR (ATR): 2965, 1651, 1596 and 1267 cm1; ESI-MS (m/z) [M+H]+=644.

Quelle