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[ CAS No. 40615-36-9 ]

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CAS No. :40615-36-9 MDL No. :MFCD00008409
Formula : C21H19ClO2 Boiling Point : 463.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :338.83 g/mol Pubchem ID :96831
Synonyms :

Safety of [ 40615-36-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P271-P272-P273-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P333+P313-P362+P364-P391-P403+P233-P405-P501 UN#:3261
Hazard Statements:H314-H317-H335-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 40615-36-9 ]

  • Upstream synthesis route of [ 40615-36-9 ]
  • Downstream synthetic route of [ 40615-36-9 ]

[ 40615-36-9 ] Synthesis Path-Upstream   1~25

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Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 48, p. 7319 - 7323
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 3, p. 370 - 371
[3] Liebigs Annalen der Chemie, 1982, # 7, p. 1398 - 1402
[4] Helvetica Chimica Acta, 1982, vol. 65, # 8, p. 2372 - 2393
[5] Nucleosides and Nucleotides, 1997, vol. 16, # 5-6, p. 815 - 820
[6] Nucleosides, Nucleotides and Nucleic Acids, 2004, vol. 23, # 11, p. 1683 - 1705
  • 2
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Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, # 5, p. 1316 - 1319
  • 3
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Reference: [1] Patent: EP1253154, 2002, A1, . Location in patent: Example 2
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YieldReaction ConditionsOperation in experiment
43 g at 25℃; for 12 h; To a solution of 308-1 (22.80 g, 99.91 mmol) in anhydrous pyridine (200 mE) was added DMTC1 (37.24 g, 109.90 mmol), and the mixture stirred at 25° C. for 12 h. The reaction was quenched with a sat. NH4C1 solution (200 mE), and extracted with EA (3x200 mE). The combined organic layers were washed with brine (2x 100 mE), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA2: 1 to 0:1) to give the desired product (43.00 g, 72.94 mmol) as a yellow foam.
Reference: [1] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 10, p. 1649 - 1658
[2] Organic letters, 2003, vol. 5, # 6, p. 917 - 919
[3] Journal of the American Chemical Society, 2001, vol. 123, # 15, p. 3405 - 3411
[4] Chemical Research in Toxicology, 2006, vol. 19, # 7, p. 968 - 976
[5] Nucleic Acids Research, 2015, vol. 43, # 11, p. 5275 - 5283
[6] Nucleosides, Nucleotides and Nucleic Acids, 2007, vol. 26, # 6-7, p. 709 - 712
[7] ChemMedChem, 2011, vol. 6, # 2, p. 309 - 320
[8] Tetrahedron Letters, 1992, vol. 33, # 1, p. 37 - 40
[9] Chemical & Pharmaceutical Bulletin, 1986, vol. 34, # 5, p. 2044 - 2048
[10] Tetrahedron Letters, 1994, vol. 35, # 29, p. 5221 - 5224
[11] Nucleosides and Nucleotides, 1995, vol. 14, # 3-5, p. 889 - 893
[12] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6824 - 6831
[13] Patent: US2009/264637, 2009, A1, . Location in patent: Page/Page column 29
[14] Bioconjugate Chemistry, 2012, vol. 23, # 3, p. 461 - 471
[15] Photochemical and Photobiological Sciences, 2013, vol. 12, # 8, p. 1366 - 1374
[16] Patent: US2015/366888, 2015, A1, . Location in patent: Paragraph 1309; 1310
[17] Patent: US2015/366887, 2015, A1, . Location in patent: Paragraph 1252-1253
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  • [ 23669-79-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1181 - 1184
  • 6
  • [ 100-66-3 ]
  • [ 98-07-7 ]
  • [ 40615-36-9 ]
YieldReaction ConditionsOperation in experiment
85.13%
Stage #1: at 30℃; for 10 h; Large scale
Stage #2: With hydrogenchloride In water at 30℃; for 3 h; Large scale
Stage #3: for 6 h; Reflux; Large scale
a.In a 500 L reactor, 75 kg of trichlorotoluene (M = 195.48, n = 383.67 mol)And 103.72 kg of anisole (M = 108.14, n = 959.17 mol)53.35 kg of catalyst aluminum chloride (M = 133.34, n = 400.1 mol) were added,The reaction temperature was controlled at 30 ,Stirring reaction 10h,The mixed reaction liquid I was obtained.b.At 30 ° C,475kg 5percent diluted hydrochloric acid was added to the reaction mixture I was loaded with 1000L reactor,Hydrolysis reaction 3h,Add dichloromethane 200kg,Stir stand still stratification,The organic phase was separated dichloromethane,Then extracted with dichloromethane 200kg * 2 times the aqueous phase,The combined organic phases were extracted with dichloromethane,Dry with anhydrous sodium sulfate for 2h.c.The methylene chloride was concentrated,The solvent methylene chloride was recovered.Oxalyl chloride 70.74 kg (M = 126.93, n = 557.32 mol)In the reflux state reaction 6h,Dropping petroleum ether 130kg,Crystallization after cooling down to 30 ,After solid-liquid separation to get crude DMT-Cl.The crude HPLC purity was 98.91percent.d.Crude DMT-Cl added 4.5 times the mass of dichloromethane, 20 times the mass of petroleum ether for recrystallization,After the solid-liquid separation obtained DMT-Cl wet product,DMT-Cl wet product dried to obtain the finished DMT-Cl 110.66kg,Finished DMT-Cl purity of 99.95percentFinished DMT-Cl yield 85.13percent.The mixed solvent was recovered,Quantitative use of gas chromatography GC and then apply.
Reference: [1] Patent: CN107056590, 2017, A, . Location in patent: Paragraph 0022; 0023; 0024; 0025; 0026; 0027; 0028-0045
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Reference: [1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 5, p. 1197 - 1207
[2] Organic Process Research and Development, 1998, vol. 2, # 6, p. 415 - 417
[3] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1989, p. 769 - 778
[4] Chemische Berichte, 1903, vol. 36, p. 2790
[5] Journal of the American Chemical Society, 1986, vol. 108, p. 3762
[6] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 7, p. 634 - 635
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1989, p. 769 - 778
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1994, # 7, p. 1463 - 1466
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Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 7, p. 634 - 635
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Reference: [1] Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1007 - 1009
[2] Tetrahedron Letters, 2002, vol. 43, # 11, p. 1983 - 1985
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 18, p. 6657 - 6665
  • 12
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  • [ 98796-51-1 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 41, p. 9273 - 9281
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  • [ 81256-88-4 ]
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Reference: [1] Patent: WO2018/156625, 2018, A1,
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Reference: [1] Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1007 - 1009
[2] Tetrahedron Letters, 2002, vol. 43, # 11, p. 1983 - 1985
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Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 49, p. 8929 - 8932
[2] Tetrahedron Letters, 1989, vol. 30, # 1, p. 71 - 74
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YieldReaction ConditionsOperation in experiment
100% at 20℃; for 3 h; Inert atmosphere An operation of dissolving 2’-Deoxy-2’-fluorouridine (3.00 g, 12.2 mmol) in dry pyridine, followed by concentrationunder reduced pressure was repeated 3 times to perform dehydrative azeotropic distillation. Thereafter, under an argonatmosphere, the reaction mixture was dissolved in dry pyridine (120 ml), 4,4’-dimethoxytrityl chloride (4.55 g, 13.4 mmol)was added, and the mixture was stirred at room temperature for 3 hr. The completion of the reaction was confirmed,and ethyl acetate (150 ml) and water (60 ml) were added to the reaction mixture to allow layer separation. The organiclayer was washed 3 times with 5percent aqueous sodium hydrogen carbonate solution (20 ml), washed with water (20 ml)and saturated brine (20 ml), and the obtained organic layer was dried over sodium sulfate. The solvent in the filtrate wasevaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate = 50:50- 0/100(v/v), containing 1percent triethylamine). The object fractions were collected and concentrated to give the title compound(8.48 g, quant).
100% at 20℃; for 3 h; Inert atmosphere (1)
Synthesis of 5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-fluorouridine
An operation of dissolving 2'-Deoxy-2'-fluorouridine (3.00 g, 12.2 mmol) in dry pyridine, followed by concentration under reduced pressure was repeated 3 times to perform dehydrative azeotropic distillation.
Thereafter, under an argon atmosphere, the reaction mixture was dissolved in dry pyridine (120 ml), 4,4'-dimethoxytrityl chloride (4.55 g, 13.4 mmol) was added, and the mixture was stirred at room temperature for 3 hr.
The completion of the reaction was confirmed, and ethyl acetate (150 ml) and water (60 ml) were added to the reaction mixture to allow layer separation.
The organic layer was washed 3 times with 5percent aqueous sodium hydrogen carbonate solution (20 ml), washed with water (20 ml) and saturated brine (20 ml), and the obtained organic layer was dried over sodium sulfate.
The solvent in the filtrate was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50-0/100 (v/v), containing 1percent triethylamine).
The object fractions were collected and concentrated to give the title compound (8.48 g, quant).
100% at 20℃; for 16 h; A solution of 2’-deoxy-2’-fluorouridine (6g, 24.37 mmol) and 4,4'-(chloro(phenyl) methylene)-bis(methoxybenzene) (9.91 g, 29.2 mmol) in pyridine (48.7 ml) was stirred at rt for 16 hours. The mixture was treated with MeOH (20 mL), concentrated to dryness and was partitioned between water (50 mL) and EtOAc (250 mL). The aqueous phase was back extracted with EtOAc (50 mL) and the combined organic layers were washed with water (50 mL) and dried over Na2SO4. The solution was concentrated to give 2’-deoxy-2’-fluoro-5’- (4’,4’-dimethoxytrityl)uridine (14g, quant.) which was used without further purification.
100% at 20℃; for 16 h; A solution of 2'-deoxy-2'-fluorouridine (6g, 24.37 mmol) and 4,4'-(chloro(phenyl) methylene)-bis(methoxybenzene) (9.91 g, 29.2 mmol) in pyridine (48.7 ml) was stirred at rt for 16 hours. The mixture was treated with MeOH (20 mL), concentrated to dryness and was partitioned between water (50 mL) and EtOAc (250 mL). The aqueous phase was back extracted with EtOAc (50 mL) and the combined organic layers were washed with water (50 mL) and dried over Na2S04 The solution was concentrated to give 2'-deoxy-2'- fluoro-5'-(4',4'-dimethoxytrityl)uridine (14g, quant.) which was used without further purification.

Reference: [1] Patent: EP2816053, 2014, A1, . Location in patent: Paragraph 0370
[2] Patent: US9371353, 2016, B2, . Location in patent: Page/Page column 78
[3] Patent: WO2016/145142, 2016, A1, . Location in patent: Page/Page column 346
[4] Patent: WO2017/155923, 2017, A1, . Location in patent: Page/Page column 161
[5] Helvetica Chimica Acta, 1997, vol. 80, # 6, p. 1952 - 1971
[6] Journal of Medicinal Chemistry, 1993, vol. 36, # 7, p. 831 - 841
[7] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 15, p. 4539 - 4543
[8] Patent: US2013/165400, 2013, A1, . Location in patent: Paragraph 0520; 0521; 0634; 0635
[9] Patent: WO2014/209979, 2014, A1, . Location in patent: Paragraph 0225; 0344
[10] Journal of Medicinal Chemistry, 2015, vol. 58, # 4, p. 1862 - 1878
[11] Patent: WO2017/189978, 2017, A1, . Location in patent: Page/Page column 325
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YieldReaction ConditionsOperation in experiment
100% at 20℃; for 16 h; A solution of 2'-deoxy-2'-fluorouridine (6g, 24.37 mmol) and 4,4'-(chloro(phenyl) methylene)-bis(methoxybenzene) (9.91 g, 29.2 mmol) in pyridine (48.7 ml) was stirred at rt for 16 hours. The mixture was treated with MeOH (20 mL), concentrated to dryness and was partitioned between water (50 mL) and EtOAc (250 mL). The aqueous phase was back extracted with EtOAc (50 mL) and the combined organic layers were washed with water (50 mL) and dried over Na2S04. The solution was concentrated to give 2'-deoxy-2'-fluoro-5'-(4',4'- dimethoxytrityl)uridine (14g, quant.) which was used without further purification.
Reference: [1] Patent: WO2017/106710, 2017, A1, . Location in patent: Page/Page column 85
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Reference: [1] Patent: US2013/267697, 2013, A1, . Location in patent: Page/Page column
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Reference: [1] ChemistryOpen, 2016, vol. 5, # 3, p. 227 - 235
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YieldReaction ConditionsOperation in experiment
97% at 0 - 20℃; Compound 129 (570 g, 1.53 mol, 1 wt, 1 vol, 1 eq) was dissolved in pyridine (2.85 L, 35.2 mol, 4.89 wt, 5.0 vols, 23 eq). The mixture was cooled to 2.6 °C and treated with 4,4’- dimethoxytrityl chloride (DMTC1; 543 g, 1.60 mol, 0.953 wt, 1.05 eq). The mixture was stirred at 0 to 5 °C for 2 h and then allowed to warm to ambient temperature. The reaction was monitored by LC/MS and complete conversion was confirmed after overnight stirring. The reaction mixture was cooled to below 5 °C and quenched by treatment with MeOH (124 ml, 3.05 mol, 0.172 wt, 0.217 vol, 2.0 eq) for 15 minutes. The mixture was co-evaporated with toluene (2.00 L, 3.04 wt, 3.51 vol) under vacuum and then diluted with a mixture of EtOAc (2.850 L, 4.5 wt, 5.0 vol) and n-heptane (2.85 L, 3.42 wt, 5.0 vol). The organic layer was washed with saturated NaHCO3 (9 wtpercent solution in water; 2.0 L, 3.5 vol). An additional EtOAc (2.85 L, 4.5 wt, 5.0 vol) was added to completely dissolve the crude product. After stirred for 5 minutes, the two layers were separated. The organic layer was washed with water (2.0 L,3.5 wt, 3.5 vol). Solid began slowly precipitating out of the organic layer. The water layer was separated. The organic layer was then concentrated to approx. 1 vol. The crude product was slurried with a mixture of n-heptane (2.00 L, 2.40 wt, 3.51 vol) and toluene (0.50 L, 0.76 wt, 0.88 vol). After stirring for 15 minutes, the pale yellow solid was collected by vacuum filtration. The filter cake was sequentially rinsed with: (1) a mixture of n-heptane (0.60 L, 0.72 wt, 1.05 vol) and toluene (0.30 L, 0.46 wt, 0.53 vol), and then (2) n-heptane (3.00 L,3.6 wt, 5.26 vol). The solid was dried with no heat for 30 minutes and then transferred to trays for drying at 50 °C in a vacuum oven overnight to give Compound 130 as pale yelllow solid (996.7 g, 1.47 mol, 1.75 wt, 97percent yield).‘H NMR (400 IVIFIz, CHLOROFORM-d) = 8.99 (s, 1H), 8.76 (s, 1H), 8.21 (s, 1H), 8.04 - 8.00 (m, 2H), 7.64 - 7.59 (m, 1H), 7.57 - 7.50 (m, 2H), 7.41 - 7.36 (m, 2H), 7.32 - 7.15 (m, 7H), 6.83 - 6.76 (m, 4H), 6.31 (dd, J= 2.5, 17.0 Hz, 1H), 5.68 (ddd, J 2.3, 4.7, 52.7 Hz, 1H), 4.88 -4.77 (m, 1H), 4.26 -4.21 (m, 1H), 3.77 (s, 6H), 3.57 (dd, J 3.1, 10.9 Hz, 1H),3.43 (dd, J= 4.1, 10.7 Hz, 1H), 2.60 (br s, 1H)
84% at 20℃; for 16 h; To a solution of N- (9-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl) tetrahydrofuran-2-yl)-9H-purin-6-yl)- benzamide (35 g, 93.7 mmol) in pyridine (180 mL) was added DMTrCI (38.12 g, 1 12.5 mmol, 1.2 eq) and the resulting mixture was stirred at RT for 16 h. The mixture was then diluted with CH2CI2 (800 mL), washed with sat NaHC03 (2x 400 mL) and brine (400 mL). The organic layer was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by S1O2 gel chromatography (petroleum ether / EtOAc=10/l to 1/4) to give the title compound as a white solid (53.0 g, 78.4 mmol, 84percent). [0291] 1H-NMR (400 MHz, DMSO-de) δ ppm 11.26 (br s, 1H), 8.74 (s, 1H), 8.62 (s, 1H), 8.05 (d, J=7.4 Hz, 2H), 7.60 - 7.72 (m, 1H), 7.48 - 7.58 (m, 2H), 7.32 (d, J=7.2 Hz, 2H), 7.14 - 7.24 (m, 7H), 6.80 (dd, J=6.2, 8.7 Hz, 4H), 6.43 (d, J=20.0 Hz, 1H), 5.73 - 5.85 (m, 1H), 5.61 (d, J=4.4 Hz, 1H), 4.76 - 4.99 (m, 1H), 4.14 (br d, J=5.4 Hz, 1H), 3.64 - 3.79 (m, 7H), 3.19 - 3.33 (m, 2H).
31.2 g at 20℃; for 3 h; To a solution of compound 8b (30 g, 80.35 mmol) in pyridine (250 mL) was added4,4’-dimethoxytrityl chloride (54.45 g,160.71 mmol). After stirring at rt for 3 h, EtOAc (1L) was added and the mixture was filtered. The organic layer was successively washed with brine (300 mL x 3), dried over anhydrous Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (MeOH in DCM = 0percent to 5percent) to give compound 8c (31.2 g) as a white solid. ESI-MS: m/z 676.3 [M + H] .
Reference: [1] Patent: WO2018/152450, 2018, A1, . Location in patent: Page/Page column 61; 62
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 15, p. 4539 - 4543
[3] Patent: WO2018/156625, 2018, A1, . Location in patent: Paragraph 0290; 0291
[4] Journal of Medicinal Chemistry, 1993, vol. 36, # 7, p. 831 - 841
[5] Tetrahedron Letters, 1998, vol. 39, # 13, p. 1657 - 1660
[6] Patent: WO2018/138685, 2018, A2, . Location in patent: Page/Page column 109; 138; 174; 176
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Reference: [1] Helvetica Chimica Acta, 1997, vol. 80, # 6, p. 1952 - 1971
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 7, p. 831 - 841
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  • [ 146954-75-8 ]
Reference: [1] Patent: EP2816053, 2014, A1,
[2] Patent: US9371353, 2016, B2,
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  • [ 103285-22-9 ]
Reference: [1] Patent: US5646265, 1997, A,
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  • [ 2140-76-3 ]
  • [ 103285-22-9 ]
Reference: [1] Monatshefte fur Chemie, 2013, vol. 144, # 4, p. 495 - 500
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 15, p. 4539 - 4543
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  • [ 134031-86-0 ]
Reference: [1] Helvetica Chimica Acta, 2000, vol. 83, # 8, p. 2023 - 2035
[2] Nucleosides and Nucleotides, 1997, vol. 16, # 7-9, p. 1657 - 1660
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