Reaktion #603622

Reaktionsgleichung

5-(4-Methoxy-benzyloxy)-1-methyl-1H-pyrazole-3-carboxylic acid

DIPEA

(2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester

DMF

EtOH

LiOH

water

HCTU

→

title compound

Ausbeute 70.5%

(2R,4R)-5-(3′-Chlorobiphenyl-4-yl)-2-hydroxy-4-{[5-(4-methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carbonyl]amino}pentanoic Acid

Ausbeute 70.5%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 15 minutes
2. 2
   SonstigeThe solvent was removed in vacuo
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature for 1 hour
4. 4
   SonstigeThe solvent was removed in vacuo
5. 5
   Sonstigethe product was purified by reverse phase chromatography

Vorschrift

5-(4-Methoxy-benzyloxy)-1-methyl-1H-pyrazole-3-carboxylic acid (118.8 mg, 453 mol) was combined with HCTU (187.3 mg, 453 μmol) and DMF (2.0 mL, 25.9 mmol). The mixture was stirred at room temperature for 15 minutes. DIPEA (225 μL, 1.3 mmol) and (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (150 mg, 430 μmol) were added and the mixture was stirred at room temperature for 15 minutes. The solvent was removed in vacuo. EtOH (1.5 mL, 25.9 mmol) was added, followed by a solution of 1 M LiOH in water (4.3 mL, 4.3 mmol). The mixture was stirred at room temperature for 1 hour. The solvent was removed in vacuo and the product was purified by reverse phase chromatography to yield the title compound (171 mg).

Quelle