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Chemical Structure| 258832-61-0 Chemical Structure| 258832-61-0

Structure of 258832-61-0

Chemical Structure| 258832-61-0

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Product Details of [ 258832-61-0 ]

CAS No. :258832-61-0
Formula : C8H11ClFN3O3S
M.W : 283.71
SMILES Code : O=C1N=C(N)C(F)=CN1[C@@H]2CS[C@H](CO)O2.[H]Cl

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Application In Synthesis of [ 258832-61-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 258832-61-0 ]

[ 258832-61-0 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 258832-61-0 ]
  • [ 143491-57-0 ]
YieldReaction ConditionsOperation in experiment
93.2% With triethylamine In methanol at 15 - 60℃; 170g of emtricitabine hydrochloride II (HPLC purity of 99.96percent), adding methanol 850mL, heating to 50 ~ 60 dissolved, cooling to 15 ~ 25 , adding dropwise 62g of triethylamine added about 6 ~ 8 minutes.The mixture was stirred at 15-25 ° C for 1 hour, concentrated in vacuo to remove methanol, 700 mL of methylene chloride was added and the mixture was stirred at 20-25 ° C for 1 hour.Filter, filter cake was added 500mL dichloromethane, atStirred at 20-25 ° C for 1 hour, filtered and the filter cake was washed twice with 250 mL of methylene chloride.138 g Emtricitabine I was obtained by vacuum drying at -0.08 ~ -0.1 MPa and 50 ~ 60 for 6 ~ 12 h. The HPLC purity was 99.94percent. The maximum single impurity was 0.04percent. The residue on ignition was 0.03percent. The yield was 93.2percent.
82% With triethylamine In methanol at 25 - 65℃; for 0.25 h; Heating / reflux Emtricitabine hydrochloride (100 g) was dissolved in methanol (500 ml). The mixture was stirred for 15 mins. Triethylamine (80 g) was added to the solution at 25- 35°C. The solution was heated to reflux and maintained at reflux temperature 60- 65°C for 60 mins. The reaction mass was cooled to 25-35°C and decolourised with activated carbon at 25-35°C. Filtrate was distilled under vacuum to thick residue below 500C. The mass was cooled to 25-35°C. Traces of methanol was removed by flushing with methylene chloride (100 ml). Methylene chloride was charged to the residue and heated to reflux. Reaction mass was maintained at reflux temperature for 2 hrs. The suspension was cooled to 250C. The reaction mass was maintained at 25- 35°C for 1 hr. Solid was collected by filtration and leached with methylene chloride (200 ml) and washed with methylene chloride (100 ml). The solid was dried at 45- 5O0C to get Emtricitabine (67 gm, 82percent). This technical grade Emtricitabine can be decolourised in IPA to get pharmaceutically accepted quality productWhile this invention has been described in detail with reference to certain preferred embodiments, it should be appreciated that the present invention is not limited to those precise embodiments. Rather, in view of the present disclosure, which describes the current best mode for practicing the invention, many modifications and variations would present themselves to those skilled in the art without departing from the scope and spirit of this invention
References: [1] Patent: CN106478618, 2017, A, . Location in patent: Paragraph 0071; 0072; 0073-0074.
[2] Patent: WO2009/84033, 2009, A2, . Location in patent: Page/Page column 10.
[3] Patent: WO2011/107920, 2011, A1, . Location in patent: Page/Page column 13.
[4] Organic Process Research and Development, 2006, vol. 10, # 3, p. 670 - 672.
 

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