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Chemical Structure| 142340-99-6
Chemical Structure| 142340-99-6
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CAS No. :142340-99-6 MDL No. :MFCD00869897
Formula : C20H32N5O8P Boiling Point : -
Linear Structure Formula :- InChI Key :WOZSCQDILHKSGG-UHFFFAOYSA-N
M.W : 501.47 Pubchem ID :60871
Synonyms :
GS 0840

Safety of [ 142340-99-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 142340-99-6 ]

* 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 [ 142340-99-6 ]
  • Downstream synthetic route of [ 142340-99-6 ]

[ 142340-99-6 ] Synthesis Path-Upstream   1~11

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Reference: [1] ChemMedChem, 2015, vol. 10, # 8, p. 1351 - 1364
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  • [ 18997-19-8 ]
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YieldReaction ConditionsOperation in experiment
75% With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 25℃; for 24 h; Example 1. Preparation of adefovir dipivoxil in an amorphous form[47] An amorphous form of adefovir dipivoxil, a raw material to prepare adefovir dipivoxil in DH-type crystalline form, was prepared as follows.[48] 30 g (0.11 mol) of 9- [2-(phosphonomethoxy)ethyl] adenine (PMEA) was dissolved in240 mL of dimethyl formamide (DMF), 42.4 g of l,8-diazabicyclo[5,4,0]undec-7-ene (DBU) was added thereto, and the mixture was stirred. 82.8 g of chloromethyl pivalate was added thereto, and the mixture was stirred at 250C for 24 hours. After confirming the termination of reaction via thin layer chromatography (TLC), 240 mL of water was added thereto, and the mixture was stirred for about 10 minutes. The mixture was subjected to extraction three times, each time with 500 mL of toluene, dried using sodium sulfate, and concentrated under reduced pressure to obtain 41.3 g of an amorphous form of adefovir dipivoxil (yield: 75percent).[49] Purity: 99.5 percent (HPLC); 1H NMR (CDCl3, ppm) 8.32 (s, IH), 7.91 (s, IH), 6.14 (s,2H, NH2), 5.64 (m, 4H), 4.38 (t, 2H, J = 4.8 Hz), 3.93 (t, 2H, J= 4.8 Hz), 3.84 (d, 2H, J = 7.5 Hz), 1.19 (s, 18H5 CH3)
57.5% With tetrabutylammomium bromide; triethylamine In 1-methyl-pyrrolidin-2-one at 65 - 75℃; for 2 h; To the flask was added adefovir 55 g,200 ml of N-methylpyrrolidone was added,The temperature was raised to 65-75 ° C,160 ml of chloromethyl pivalate was added,Triethylamine 90ml,Tetra-n-butylammonium bromide,Reaction 2h,High-performance liquid chromatography to detect the main peak area of 66percent for the reaction completely,Ethyl acetate (700 ml)Stirring dissolved 30min,filter,And washed three times with 220 ml ethyl acetate each time until the filter cake was white,The filtrate was washed with saturated brine (550 ml) three times,The aqueous phase was discarded,The organic phase was dried over 110 g of anhydrous sodium sulfate for 2 h,filter,Removal of anhydrous sodium sulfate,And the filter cake was washed with 50 ml of ethyl acetate,The filtrate was concentrated to a pale yellow viscous liquid at 40-50 ° C under reduced pressure,10-15 ° C by adding anhydrous ether 600ml,There is a crystal precipitation,filter,50 ml of dry ether,40-50 vacuum drying 4h was adefovir dipivoxil 58g,Yield 57.5percent.HPLC purity:Greater than 99percent.
52% With 1-methyl-pyrrolidin-2-one; triethylamine In ethanol; N,N-dimethyl-formamide at 60 - 70℃; for 1 h; Large scale comprising the steps of: (1) In a clean glass kettle, 5 L of DMF, 5 L of N-methylpyrrolidone and 0.5 L of absolute ethanol, lkg of PMEA And 4.5kg of chloropentyl pivalate, stirring to 60 ~ 70 ° C, dropping 3 kg of triethylamine, 1 h after the drop is completed, and then reaction 2.5 After the hour, the reaction was detected by HPLC, and the amount of PMEA in the reaction solution was less than 0.5percent, and the reaction was terminated. (2) 10 L of ethyl acetate was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour, filtered, and washed with 10 L of ethyl acetate The filter cake was washed with 10 L of a 20percent sodium chloride solution, the aqueous phase of the washing solution was discarded, and the organic phase was washed with anhydrous Calcium chloride lkg dry 2 h, filter, remove the calcium chloride solid, the filtrate. (3) The filtrate was concentrated under reduced pressure at 45 ° C, and then 1L of chloroform was dissolved under stirring at 5 to 10 ° C, and the mixture was transferred to another A reaction kettle, in the 5 ~ 10 ° C dropping 12L methyl tert-butyl ether, 10-15 min after the white crystal precipitation, stirring crystallization 6-7 H, filter, 45 ° C vacuum drying Adefovir dipivoxil finished product 0.96kg: molar yield of 52percent, by HPLC, the content of 99.7percent, containing impurities Adefovir monoester 0.19percent. The product is good crystal, easy to dry, good stability
34.9% With triethylamine In 1-methyl-pyrrolidin-2-one at 60℃; for 2 h; A mechanical stirrer, reflux condenser and thermometer were installed in a 50 L dry reaction flask. (3.66 mol) of PMEA and 3.6 L of N-methylpyrrolidone (NMP) were added thereto in succession, followed by the addition of 2.2 kg (14.67 mol) of chloromethyl pivalate and triethylamine 1. lkg . After heating to 60 ° C for 2 hours, the mixture was cooled to room temperature and extracted three times with 20 L of isopropyl acetate. The filtrate was washed with water and the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 5 L of acetone, With stirring, 25 L of isopropyl ether was slowly added to give a solid product, and stirring was continued for 5 hours, followed by filtration. (1/9, ν / ν). After adding the right amount of acetone to dissolve the filter cake, add appropriate amount of activated carbon, stir for 30 min and filter to the clean area crystallization tank, add isopropyl ether to crystallize completely, filter and use acetone / After sufficient washing, vacuum drying (50 ° C, 20 mmHg)To obtain 767 g of adefovir dipivoxil as an off-white powder with a purity of 99.1percent and a total yield of 34.9percent.

Reference: [1] Patent: WO2010/110506, 2010, A1, . Location in patent: Page/Page column 7
[2] Patent: CN105646586, 2016, A, . Location in patent: Paragraph 0034; 0035; 0036; 0037; 0038; 0039; 0040-0044
[3] Patent: CN106188140, 2016, A, . Location in patent: Paragraph 0019; 0020; 0021; 0022
[4] Patent: CN104387421, 2016, B, . Location in patent: Paragraph 0035-0037
[5] Journal of Medicinal Chemistry, 1994, vol. 37, # 12, p. 1857 - 1864
[6] Patent: WO2010/120074, 2010, A2, . Location in patent: Page/Page column 10
[7] Patent: EP2327708, 2011, A2, . Location in patent: Page/Page column 10
[8] Patent: US2012/238753, 2012, A1, . Location in patent: Page/Page column 3
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YieldReaction ConditionsOperation in experiment
32.6% With triethylamine In 1-methyl-pyrrolidin-2-one at 30 - 60℃; for 16 h; In a 2L reaction flask,Respectively, adefovir 40.2g (0. 147mol),N-methylpyrrolidone 80 g (0.807 mol) and triethylamine (35 mL) were added 110 g of chloropentyl valerate (0 • 73 lmo 1)30 ~ 40 ° C stirring reaction 12h, and then heating 50 ~ 60 ° C stirring 4h;Cooling to room temperature, adding ethyl acetate 608mL, stirring at room temperature 1 ~ 2h; filtration,The filter cake was washed with ethyl acetate and the filtrate was washed with saturated aqueous sodium chloride solution. The resulting organic layer was dried over anhydrous sodium sulfate,The mixture was allowed to stand overnight; the filtrate was concentrated under reduced pressure to give an oil,Add ethanol 70ml, stirring lOmin, stirring evenly, adding isopropyl ether, crystallization, this time the solution becomes turbid, continue stirring 7 ~ 8h; filter, anhydrous ethanol washing, the white solid powder, that is, the target compound Ade Fuwei ester, yield 32.6percent.
Reference: [1] Patent: CN106699814, 2017, A, . Location in patent: Paragraph 0026-0027
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Reference: [1] Patent: WO2007/13085, 2007, A1, . Location in patent: Page/Page column 10-11
[2] Patent: US2009/12292, 2009, A1, . Location in patent: Page/Page column 4
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  • [ 18997-19-8 ]
  • [ 116384-53-3 ]
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Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 869 - 881
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  • [ 18997-19-8 ]
  • [ 106941-25-7 ]
  • [ 323201-04-3 ]
  • [ 142340-99-6 ]
Reference: [1] Patent: EP2330107, 2011, A2, . Location in patent: Page/Page column 6
[2] Patent: US2011/207930, 2011, A1, . Location in patent: Page/Page column 4
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  • [ 53064-79-2 ]
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Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 25, p. 4958 - 4965
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  • [ 153235-86-0 ]
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Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 25, p. 4958 - 4965
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  • [ 66224-66-6 ]
  • [ 142340-99-6 ]
Reference: [1] Patent: US2012/238753, 2012, A1,
[2] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 869 - 881
[3] Patent: CN106699814, 2017, A,
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  • [ 707-99-3 ]
  • [ 142340-99-6 ]
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 869 - 881
[2] Patent: CN104387421, 2016, B,
[3] Patent: CN106699814, 2017, A,
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  • [ 116384-53-3 ]
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Reference: [1] Patent: US2012/238753, 2012, A1,
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