반응 #557094

반응 방정식

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

methanesulfonyl chloride

→

title compound

수율 99.4%

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

수율 99.4%

용매

pyridine

반응 조건

후처리

1. 1
   온도cooled to ambient temperature
2. 2
   workup.STIRRINGto stir for 18 hours
3. 3
   농축The mixture is concentrated under reduced pressure
4. 4
   기타to give a residue
5. 5
   기타The residue is partitioned between ethyl acetate and 1N aqueous HCl (2×50 mL)
6. 6
   기타The organic layer is separated
7. 7
   건조dried over magnesium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated under reduced pressure

실험 절차

Di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate (4.6 g, 8.10 mmol) in pyridine (60 mL) is cooled to 0° C. To this mixture is added methanesulfonyl chloride (1.88 ml, 24.31 mmol). The mixture is warmed to 40° C. and stirred for 1 hour, and cooled to ambient temperature and allowed to stir for 18 hours. The mixture is concentrated under reduced pressure to give a residue. The residue is partitioned between ethyl acetate and 1N aqueous HCl (2×50 mL). The organic layer is separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound (5.2 g, 8.05 mmol, 99.4% yield): MS (m/z): 643.6 (M−H).

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