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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 : |
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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: | Ⅱ |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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] . |