Reaktion #603637

Reaktionsgleichung

5-Hydroxy-1-methyl-1H-pyrazole-3-carboxylic acid

HCTU

DIPEA

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

EtOH

LiOH

water

→

title compound

Ausbeute 14.4%

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

Ausbeute 14.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting mixture was stirred overnight at room temperature
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hour
3. 3
   SonstigeThe mixture was evaporated under reduced pressure
4. 4
   Sonstigepurified by preparative HPLC

Vorschrift

5-Hydroxy-1-methyl-1H-pyrazole-3-carboxylic acid (19.6 mg, 138 μmol) was combined with HCTU (56.9 mg, 138 μmol) in DMF. The mixture was stirred for 10 minutes at room temperature before adding DIPEA (72 μL, 413 μmol) and (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (50 mg, 0.1 mmol). The resulting mixture was stirred overnight at room temperature. EtOH (402 μL, 6.9 mmol) and 1 M LiOH in water (1.1 mL, 1.1 mmol) was added and the mixture was stirred at room temperature for 1 hour. The mixture was evaporated under reduced pressure and purified by preparative HPLC to yield the title compound (6.4 mg). MS m/z [M+H]+ calc'd for C22H22ClN3O5, 444.12. found 444.4.

Quelle