반응 #2260174

반응 방정식

di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate

Potassium carbonate

1H-1,2,4-triazole-3-thiol

dimethylformamide

→

title compound

수율 69.5%

Di-tert-butyl (1R,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]hexane-2,6-dicarboxylate

수율 69.5%

용매

sodium bicarbonate

반응 조건

후처리

1. 1
   workup.STIRRINGstirred at 85° C
2. 2
   workup.WAITAfter 2 days
3. 3
   온도cool
4. 4
   기타the reaction to room temperature
5. 5
   추출extract with ethyl acetate (3×)
6. 6
   세척The combined organics are washed with water, brine
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure
9. 9
   기타to give a residue
10. 10
    기타The residue is purified by flash chromatography
11. 11
    세척eluting with 5-75% ethyl acetate in hexanes

실험 절차

Potassium carbonate (1.45 g, 10.50 mmol) is added to 1H-1,2,4-triazole-3-thiol (424.79 mg, 4.20 mmol) and dimethylformamide (10.50 mL, 9.93 g, 135.80 mmol) at room temperature and stirred. After 5 minutes, di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (1.40 g, 2.10 mmol) is added to the reaction and stirred at 85° C. After 2 days, cool the reaction to room temperature, dilute with saturated sodium bicarbonate, then extract with ethyl acetate (3×). The combined organics are washed with water, brine, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography eluting with 5-75% ethyl acetate in hexanes to give the title compound (978.0 mg, 1.46 mmol, 69%). MS (m/z): 671/669 (M−1).

출처