تفاعل #796111

معادلة التفاعل

39C

Benzyl 5-((((R)-2-(4-bromo-2-methylphenyl)propoxy)carbonyl)amino)-3-fluoro-2-(((S)-tetrahydrofuran-3-yl)oxy)benzyl(methyl)carbamate

5,5,5′,5′-tetramethyl-2,2′-bi(1,3,2-dioxaborinane)

KOAc

→

39D

المردود 55.7%

(4-((R)-1-(((3-((((Benzyloxy)carbonyl)(methyl)amino)methyl)-5-fluoro-4-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)carbamoyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid

المردود 55.7%

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThe tube was filled with Ar
2. 2
   أخرىsealed
3. 3
   أخرىThe mixture was quenched with H2O
4. 4
   استخلاصextracted with EtOAc (3×)
5. 5
   ترشيحThe combined organic layers was filtered though silica gel
6. 6
   تركيزconcentrated
7. 7
   أخرىThe residue was purified by prep HPLC

الإجراء التجريبي

To a reaction tube was added 39C (770 mg, 1.223 mmol), 5,5,5′,5′-tetramethyl-2,2′-bi(1,3,2-dioxaborinane) (332 mg, 1.468 mmol), KOAc (300 mg, 3.06 mmol), and Pd(dppf)Cl2 (201 mg, 0.245 mmol) in DMSO (10 ml). The tube was filled with Ar, sealed and stirred at 85° C. for 2 h. The mixture was quenched with H2O, and extracted with EtOAc (3×). The combined organic layers was filtered though silica gel and concentrated. The residue was purified by prep HPLC to give 39D (405 mg, 0.681 mmol, 55.7% yield) as a tan solid. MS (ESI) m/z: 595.4 (M+H)+.

المصدر