반응 #557103

반응 방정식

di-tert-butyl (1S,2R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-methylidene-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate

3,4-difluorobenzenethiol

triethylamine

→

title compound

수율 141.0%

Di-tert-butyl (1S,2R,3S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-{[(3,4-difluorophenyl)sulfanyl]methyl}-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate

수율 141.0%

용매

toluene

반응 조건

후처리

1. 1
   workup.WAITAfter twelve hours
2. 2
   온도the reaction was cooled to room temperature
3. 3
   세척washed sequentially with 2N aqueous NaOH (pH=10)
4. 4
   건조1N HCl (pH=4), dried over MgSO4
5. 5
   농축concentrated in vacuo
6. 6
   기타to yield a residue
7. 7
   기타Triturate the residue with hexane (1 L)
8. 8
   기타remove the solvent

실험 절차

A suspension of di-tert-butyl (1S,2R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-methylidene-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate (350.00 g, 826.43 mmol) in toluene (2.95 L) is treated with 3,4-difluorobenzenethiol (172.49 g, 1.18 mol) and triethylamine (205.61 mL, 149.28 g, 1.48 mol) at 25° C. The mixture is stirred at 80° C. After twelve hours, the reaction was cooled to room temperature, washed sequentially with 2N aqueous NaOH (pH=10) and aqueous. 1N HCl (pH=4), dried over MgSO4, and concentrated in vacuo to yield a residue. Triturate the residue with hexane (1 L) and remove the solvent to yield the title compound (664 g, 100% yield).

출처