تفاعل #1937311

معادلة التفاعل

tert-butyl (S)-1-(4-bromophenyl)ethyl(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)carbamate

cyclohexanecarboxamide

cesium carbonate

XANTPHOS

→

solid

المردود 58.9%

tert-butyl (S)-1-(4-(cyclohexanecarboxamido)phenyl)ethyl(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)carbamate

المردود 58.9%

ظروف التفاعل

المعالجة

1. 1
   أخرىIn a 5 ml microwave reaction
2. 2
   أخرىThe vial was sealed
3. 3
   أخرىevacuated
4. 4
   أخرىpurged with dry nitrogen three times
5. 5
   workup.ADDITIONbefore adding dioxane (1.6 mL)
6. 6
   درجة الحرارةAfter cooling the reaction
7. 7
   workup.ADDITIONwas diluted with EtOAc (10 mL)
8. 8
   غسيلwashed with water (10 mL)
9. 9
   أخرىAfter separation
10. 10
    استخلاصthe aqueous phase was extracted with EtOAc (3×10 mL)
11. 11
    تجفيفCombined organics were dried over Na2SO4
12. 12
    ترشيحfiltered
13. 13
    تركيزconcentrated
14. 14
    أخرىThe crude material was purified through silica gel column chromatography (EtOAc in Heptane 12 to 100%)

الإجراء التجريبي

In a 5 ml microwave reaction vial was added tert-butyl (S)-1-(4-bromophenyl)ethyl(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)carbamate (101 mg, 0.2 mmol), cyclohexanecarboxamide (30 mg, 0.24 mol), cesium carbonate (91 mg, 0.28 mmol), XANTPHOS (7 mg, 0.012 mmol, strem chemicals), and Pd2(dba)3 (4 mg, 0.02 mmol). The vial was sealed, evacuated and purged with dry nitrogen three times before adding dioxane (1.6 mL). The reaction mixture was heated to 100° C. for 16 hours in an oil bath. After cooling the reaction was diluted with EtOAc (10 mL) and washed with water (10 mL). After separation, the aqueous phase was extracted with EtOAc (3×10 mL). Combined organics were dried over Na2SO4, filtered and concentrated. The crude material was purified through silica gel column chromatography (EtOAc in Heptane 12 to 100%) to give a white solid (65 mg, 58.9% yield).

المصدر