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Step E: Preparation of zanamivirIn a reaction vessel, 7.3 g of the solid residue, from step D, was taken and to it 7.3 g of ammonium formate along with 140 ml ammonia added at 25C - 3O0C. The reaction mass was heated to 900C for 3 hrs. 0.7 g of charcoal was added to this reaction mass and content was stirred for about 1 hr. Then the mass was cooled to 20C - 25C and filtered. The filtrate was concentrated at 600C under vacuum to obtain residue in which 100 ml of methanol was added and stirred. The resulting solid was filtered and dried under vacuum to yield 5.0 g of the title compound (yield - 69%, HPLC purity - 85%).
69%
In a reaction vessel, 7.3 g of the solid residue, from step D, was taken and to it 7.3 g of ammonium formate along with 140 ml ammonia added at 25 C.-30 C. The reaction mass was heated to 90 C. for 3 hrs. 0.7 g of charcoal was added to this reaction mass and content was stirred for about 1 hr. Then the mass was cooled to 20 C.-25 C. and filtered. The filtrate was concentrated at 60 C. under vacuum to obtain residue in which 100 ml of methanol was added and stirred. The resulting solid was filtered and dried under vacuum to yield 5.0 g of the title compound (yield-69%, HPLC purity-85%).
With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 5 - 20℃; for 0.5h;
Process for the preparation of 5-(acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-P-glycero-D-galacto-non-enonic acid (Formula I); Charged DBU (22.48 gm) in a vessel containing 5-acetamido-4-guanidino-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (as prepared in example-2) slowly at temp 5-10 C. Subsequently, the temperature was raised up to RT and maintained for 30 min. The reaction mass was washed with MDC and subsequently, acetone was added. The product thus obtained was isolated. The compound was filtered, washed with acetone and dried under reduced pressure at 50 C. The yield was 6.7 g (61.3%). HPLC Purity-99.5%
61.3%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 5 - 25℃; for 0.5h;Product distribution / selectivity;
Example-6: Process for the preparation of 5-(acetylamino)-4- [(aminoiminomethyl)aminol-2,6-anhvdro-3,4,5-trideoxy-D-glycero-D-galacto-non- enonic acid (Formula I) Charged DBU (22.48gm) in a vessel containing 5-acetamido-4-guanidino-6- (l,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (as prepared in example- 2) slowly at temp 5-10 C. Subsequently, the temperature was raised up to RT and maintained for 30 min. The reaction mass was washed with MDC and subsequently, acetone was added. The product thus obtained was isolated. The compound was filtered, washed with acetone and dried under reduced pressure at 50 C.The yield was 6.7 g (61.3 %). HPLC Purity - 99.5%
cellulose acetate and polyethylene glycol 400 are added to acetone and mixed thoroughly to form a polymer solution.
Yield
Reaction Conditions
Operation in experiment
With pyrographite; In water; isopropyl alcohol; at 20 - 90℃;Purification / work up;
Step F: Purification of <strong>[139110-80-8]zanamivir</strong>Crude <strong>[139110-80-8]zanamivir</strong> (5 g), from earlier step, was stirred with 50 ml of water and heated to 900C to get suspension. To it 4 g charcoal was added and filtered hot through hyflo to get a clear solution. To the clear filtrate 15 ml of isopropyl alcohol was added dropwise. The solid thus obtained was filtered, washed with isopropyl alcohol and dried under vacuum at 60C to obtain 2.5 g of pure <strong>[139110-80-8]zanamivir</strong> (HPLC purity - 99.5%).
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