تفاعل #628691

معادلة التفاعل

(R)-3-{N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)-N′-[3-(2-fluorophenyl)isoxazole-5-carbonyl]hydrazino}-2-hydroxypropionic acid

EDC HCl

HOBt hydrate

DCM

2,2,3,3,3-Pentafluoro-1-propanol

→

title compound

المردود 12.8%

(R)-3-{N-(5′-Chloro-2′-fluorobiphenyl-4-ylmethyl)-N′-[3-(2-fluorophenyl)isoxazole-5-carbonyl]hydrazino}-2-hydroxypropionic acid 2,2,3,3,3-pentafluoropropyl Ester

المردود 12.8%

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 1 hour
2. 2
   تركيزthen concentrated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in AcOH (2 mL)
4. 4
   ترشيحfiltered
5. 5
   أخرىpurified by reverse phase prep HPLC

الإجراء التجريبي

A mixture of (R)-3-{N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)-N′-[3-(2-fluorophenyl)isoxazole-5-carbonyl]hydrazino}-2-hydroxypropionic acid (30.0 mg, 57 μmol), EDC HCl (65.4 mg, 341 μmol), and HOBt hydrate (52.2 mg, 341 μmol) in DCM (0.5 mL, 8 mmol) was stirred at room temperature for 10 minutes. 2,2,3,3,3-Pentafluoro-1-propanol (45.3 μL, 455 μmol) was added and the resulting mixture was stirred at room temperature for 1 hour then concentrated. The residue was dissolved in AcOH (2 mL), filtered, and purified by reverse phase prep HPLC to yield the title compound (4.8 mg, purity 90.2%) as a TFA salt. MS m/z [M+H]+ calc'd for C29H21ClF7N3O5, 660.11. found 660.3.

المصدر