반응 #557104

반응 방정식

Water

hydrogen chloride

water

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

NaOH

→

title compound

수율 87.0%

(1S,2R,3S,4S,5R,6R)-2-Amino-3-{[(3,4-difluorophenyl)sulfanyl]methyl}-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid

수율 87.0%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   온도the reaction is then cooled to 25° C.
2. 2
   workup.STIRRINGstirred for 12 hours
3. 3
   workup.STIRRINGThe resulting mixture is stirred at 10° C. for 30 minutes whereupon the precipitate
4. 4
   여과is collected by filtration
5. 5
   세척washed with water (1 L) and methyl tert-butyl ether (1 L)
6. 6
   기타dried for 2 hours at 25° C.

실험 절차

Water (1.10 L) and 12.18M hydrogen chloride in water (789.88 mL, 9.62 mol) is added to a solution of di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-{[(3,4-difluorophenyl)sulfanyl]methyl}-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate (550.00 g, 962.07 mmol) in 1,4-dioxane (192.41 mL). The resulting slurry is stirred at 100° C. After 12 hours, the reaction is then cooled to 25° C., stirred for 12 hours, and then basified with NaOH (50% wt/wt) to pH=2.65. The resulting mixture is stirred at 10° C. for 30 minutes whereupon the precipitate is collected by filtration, washed with water (1 L) and methyl tert-butyl ether (1 L), and dried for 2 hours at 25° C., and then at 60° C. in a oven until constant weight to yield the title compound (300 g, 87% yield). MS (m/z): 360 (M+1).

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