Reaktion #603640

Reaktionsgleichung

LiOH

water

5-Hydroxy-1-pyridin-2-yl-1H-pyrazole-3-carboxylic acid

HCTU

(2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid 5-methyl-2-oxo[1,3]dioxol-4-ylmethyl ester

DIPEA

DMF

→

title compound

Ausbeute 58.4%

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

Ausbeute 58.4%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 15 minutes
2. 2
   SonstigeThe reaction was evaporated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in EtOH
4. 4
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 1 hour
5. 5
   Sonstigeevaporated under reduced pressure
6. 6
   SonstigeThe residue was purified by preparative HPLC

Vorschrift

5-Hydroxy-1-pyridin-2-yl-1H-pyrazole-3-carboxylic acid (59.0 mg, 287 μmol) and HCTU (131 mg, 316 μmol) were combined in DMF (1.3 mL, 17.2 mmol). and stirred at room temperature for 15 minutes. (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid 5-methyl-2-oxo[1,3]dioxol-4-ylmethyl ester (100 mg, 0.3 mmol) and DIPEA (150 μL, 862 μmol) were added, and the resulting mixture was stirred at room temperature for 15 minutes. The reaction was evaporated under reduced pressure. The residue was dissolved in EtOH and a solution of 1 M LiOH in water (1.4 mL, 1.4 mmol) was added. The resulting mixture was stirred at room temperature for 1 hour, then evaporated under reduced pressure. The residue was purified by preparative HPLC to yield the title compound (85 mg). MS m/z [M+H]+ calc'd for C26H23ClN4O5, 507.14. found 507.1.

Quelle