반응 #557098

반응 방정식

(1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid

sodium bicarbonate

dichloromethane

chloromethyl chlorosulfate

→

title compound

수율 47.0%

Bis(chloromethyl)(1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate

수율 47.0%

용매

water

water

반응 조건

후처리

1. 1
   추출extracted with dichloromethane
2. 2
   건조The combined organics are dried over magnesium sulfate
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타to give a residue
6. 6
   기타The residue is purified by flash chromatography (20-35% ethyl acetate/hexane)

실험 절차

To a stirring mixture of (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (2.4 g, 5.27 mmol), tetra(n-butyl)ammonium bisulfate (178.90 mg, 526.89 μmoles), and sodium bicarbonate (3.54 g, 42.15 mmol) in dichloromethane (13.2 mL) and water (13.2 mL) is added chloromethyl chlorosulfate (1.20 mL, 11.59 mmol). The mixture is stirred at ambient temperature for 18 hours. The reaction is poured over water and extracted with dichloromethane. The combined organics are dried over magnesium sulfate, filtered and concentrated to give a residue. The residue is purified by flash chromatography (20-35% ethyl acetate/hexane) to give the title compound (1.37 g, 2.48 mmol, 47% yield). MS (m/z): 574.0 (M+Na).

출처