Reacción #158840

Ecuación de reacción

1-(2′-acetylsulfamoylbiphenyl-4-ylmethyl)-5-propyl-1H-pyrazole-3-carboxylic acid

HATU

DIPEA

DMF

(2R,3R)-3-amino-2-hydroxy-4-phenylbutyric acid

→

title compound

Rendimiento 97.0%

(2R,3R)-3-(1-((2′-(N-Acetylsulfamoyl)biphenyl-4-yl)methyl)-5-propyl-1H-pyrazole-3-carboxamido)-2-hydroxy-4-phenylbutanoic Acid

Rendimiento 97.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe mixture was concentrated
2. 2
   workup.DISSOLUTIONre-dissolved in water/MeCN/TFA
3. 3
   Otropurified

Procedimiento

A solution of 1-(2′-acetylsulfamoylbiphenyl-4-ylmethyl)-5-propyl-1H-pyrazole-3-carboxylic acid (250 mg, 570 μmol), HATU (215 mg, 566 μmol) and DIPEA (592 μL, 3.4 mmol) in DMF (18 mL, 230 mmol) was stirred to pre-activate the acid. After 15 minutes, (2R,3R)-3-amino-2-hydroxy-4-phenylbutyric acid (110 mg, 566 μmol) was added. The resulting solution was stirred at 45° C. overnight. The mixture was concentrated, re-dissolved in water/MeCN/TFA and purified using reverse phase liquid chromatography to yield the title compound (197 mg, 97% purity). MS m/z: [M+H]+ calcd for C32H34N4O7S, 619.22. found 619.6.

Fuente