반응 #48827

반응 방정식

tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

triethylamine

→

oil

수율 39.0%

tert-Butyl 3-({3-[4-(ethoxycarbonyl)phenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

수율 39.0%

용매

DCM

반응 조건

후처리

1. 1
   기타for 7 hours
2. 2
   기타Reaction mixture
3. 3
   여과filtered through diatomaceous earth
4. 4
   세척was washed with DCM (×3)
5. 5
   농축Filtrate concentrated in vacuo
6. 6
   세척washed with 1M hydrochloric acid, saturated sodium hydrogen carbonate, saturated brine
7. 7
   건조dried (MgSO4)
8. 8
   여과Filtered
9. 9
   농축filtrate concentrated in vacuo
10. 10
    기타chromatographed (0-50% ethyl acetate/isohexane)

실험 절차

tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate (391 mg, 1 mmol), ethyl-4-boronic acid benzoate (388 mg, 2.0 equiv), copper (II) acetate (363 mg, 2.0 equiv) and triethylamine (0.7 mL; 5.0 equiv) were suspended in dry DCM over freshly activated powdered 4A molecular sieves (ca. 1 g) for 7 hours under an ambient atmosphere. Reaction mixture filtered through diatomaceous earth was washed with DCM (×3). Filtrate concentrated in vacuo, taken up in ethyl acetate and washed with 1M hydrochloric acid, saturated sodium hydrogen carbonate, saturated brine and dried (MgSO4). Filtered, filtrate concentrated in vacuo and chromatographed (0-50% ethyl acetate/isohexane) to give a brown oil (210 mg, 39%).

출처