| 99% |
With sodium hydrogencarbonate; sodium bromide In dichloromethane at 20℃; Electrochemical reaction; |
|
| 98% |
With chromium(VI) oxide; periodic acid In water; acetonitrile at 0℃; |
|
| 98% |
With periodic acid; pyridinium chlorochromate In acetonitrile at 0 - 20℃; for 2h; |
|
| 98% |
With dihydrogen peroxide In water at 80 - 120℃; for 0.5h; Microwave irradiation; Green chemistry; |
|
| 98% |
With oxone; 1-(2-(3-carboxy-4-iodophenoxy)ethyl)-3-methyl-1H-imidazol-3-ium hexafluorophosphate In water at 70℃; for 4h; |
|
| 95% |
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.6h; Heating; |
|
| 95% |
With trinitratocerium(IV) bromate for 0.8h; Heating; |
|
| 95% |
With 1-methyl-1H-imidazole; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen In acetonitrile at 20℃; for 1h; |
|
| 94% |
With periodic acid In acetonitrile at 20℃; for 1h; |
|
| 93% |
With ammonium dichromate(VI); silica gel; zirconium(IV) chloride In hexane for 1.7h; Heating; |
|
| 93% |
With prolinium chlorochromate In hexane for 3h; Heating; |
|
| 93% |
With iodoxybenzene; bromine; sodium nitrite In water at 55℃; for 1h; |
|
| 93% |
With dihydrogen peroxide In water at 90℃; for 6h; |
|
| 92% |
With tungstate anion confined in hydrophilic/hydrophobic nanomaterials functionalized bronsted acidic imidazolium-based ionic liquid; air In water at 90℃; for 18h; |
General procedure for selective aerobic oxidation of alcohols using PMO-IL-WO42- materials
General procedure: A 25 mL single-necked round bottomed flask equipped with a condenser was charged with alcohol (10 mmol) and water (5 mL) were added and stirred. PMO -IL-WO42- (0.01 g) was then added to the above solution and the resulting mixture was stirred at 90 °C under atmospheric air pressure for the required time. The progress of the reaction was monitored by TLC and/or gas chromatography using standard addition method. After completion of the reaction, the mixture was allowed to cool down to room temperature and the catalyst was successfully filtrated, washed with ethyl acetate (2 x 10 mL) and dried under vacuum for the next run. Then, the filtrate was first washed with water, dried over magnesium sulfate, and the solvent concentrated with evaporation under vacuum to give the corresponding carbonyl compounds. |
| 91% |
With silica gel supported bis(trimethylsilyl) chromate In dichloromethane at 40℃; for 0.5h; |
|
| 90% |
With ammonium dichromate(VI); magnesium hydrogen sulfate; silica gel at 20℃; for 0.166667h; |
|
| 90% |
With potassium bromate; tetrachlorosilane; silica gel In hexane for 1.16667h; Heating; |
|
| 90% |
With tris[trinitratocerium(IV)] paraperiodate at 90℃; for 0.33h; |
|
| 90% |
With ferric nitrate; barium(II) chloride at 90℃; for 0.416667h; |
|
| 88% |
With periodic acid; pyridinium chlorochromate In acetonitrile at 0℃; for 1h; |
|
| 87% |
With Burgess Reagent; dimethyl sulfoxide at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; |
|
| 86% |
With ammonium dichromate(VI); aluminum(III) hydrogen sulfate; silica gel at 20℃; for 1.2h; |
|
| 85% |
With pyridine; trichloroisocyanuric acid In acetone for 0.333333h; |
|
| 85% |
Stage #1: 3-phenyl-2-propanol With (-N(SO2C8F17)-(biphenyl-2,2'-diyl)-O-)AlCH3 In toluene at 21℃; for 0.5h;
Stage #2: With pivalaldehyde In toluene at 21℃; for 3h; Further stages.; |
|
| 85% |
With C29H35Cl2IrN2O2; sodium acetate In 2,2,2-trifluoroethanol for 20h; Inert atmosphere; Reflux; Schlenk technique; |
|
| 84% |
With pyridinium chlorochromate In dichloromethane at 0℃; for 3h; |
32.A A. l-phenylpropan-2-one
A. l-phenylpropan-2-one [00367] A solution of l-phenylpropan-2-ol (2.72 g, 20 mmol) in CH2CI2 (20 mL) was added pyridinium chlorochromate (PCC, 5.4 g, 25 mmol) at 0 °C and the mixture was stirred for 3 h. The mixture was concentrated and purified by flash column chromatography (PE/EtOAc = 20: 1) to give the title compound (2.3 g, 84%) as a yellow oil. |
| 83% |
With pyridine; Tributylphosphine oxide; oxygen; palladium diacetate In toluene at 80℃; for 24h; Molecular sieve; |
|
| 83% |
With iron(III) chloride; 1,1,1,3',3',3'-hexafluoro-propanol; oxygen; nitric acid at 20℃; for 5h; |
|
| 80% |
With sodium carbonate; acetone; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 90℃; for 17h; |
|
| 78% |
Stage #1: 3-phenyl-2-propanol With bis(trichloromethyl) carbonate; 4-(2-(2-(methylsulfinyl)ethyl)-4-nitrophenyl)morpholine In dichloromethane at -15℃; for 1h; Inert atmosphere;
Stage #2: With triethylamine In dichloromethane at -15℃; Inert atmosphere; |
Typical procedure for the oxidation of alcohols
General procedure: A solution of BTC (0.41 g, 1.39 mmol) in dry CH2Cl2 (5 mL) was cooled in an ice-salt bath under an atmosphere of N2. A solution of I (1.24 g, 4.17 mmol) in dry CH2Cl2 (5 mL) was added dropwise for 0.5 h, at -15 °C. Stirring was continued for 0.5 h, and a solution of benzyl alcohol (0.3 g, 2.78 mmol) in dry CH2Cl2 (5 mL) was added dropwise for 0.5 h, at-15 °C. After stirring for 0.5 h, Et3N (0.84 g, 8.34 mmol) was added slowly while the temperature should be controlled below -15 °C. When the reaction was completed, 10% HCl solution in water was added dropwise until the pH of the reaction solution reached 2 under ice bath. The mixture was extracted with n-hexane or petroleum ether (10 mL x 2),decanted. The product was acquired after organic layer was concentrated and purified by flash chromatography (SiO2; n-hexane). (0.27 g, 92%). The water layer was used for the recovery of V and the excess I. |
| 77% |
Stage #1: 3-phenyl-2-propanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; Inert atmosphere;
Stage #2: With triethylamine In dichloromethane at 20℃; Cooling; Inert atmosphere; |
|
| 76% |
With Dess-Martin periodane In dichloromethane at 20℃; for 12h; |
20.1 Step 1 phcnylpropan-2-one
Step 1 Dess-Martin reagent (9.3 g, 22.0 mniol) was added into a solution of I -phenylpropan-2-ol (2.0 g, 15 mmol) in DCM (20 mL) at room temperature. The mixture was stirred at room temperature for 12 his and washed with Na2S2O3 ag. solution (20 mL), NaHCO3 aq. solution (20 mE). The organic phase was dried over anhydrous Na2SO4 and then filtered. The filtrate was concentrated and theresidue was purified by flash column chromatography on silica gel eluting with 20% EtOAc in hexanes to give the desired product (1.5 g, 76% yield) as colorless oil. ‘H NMR (400 MHz, CDC13) 6 7.35 -7.32 (m, 211), 7.29- 7.27 (m, 111), 7.25 - 7.19 (m, 2H), 3.69 (s, 2H), 2.15 (s, 311). |
| 75% |
With potassium bromide In water; acetonitrile at 20℃; for 12h; |
|
| 72% |
With caesium carbonate In para-xylene for 24h; Reflux; |
|
| 70% |
With potassium bromate; zirconium(IV) oxychloride In acetonitrile for 0.5h; Heating; |
|
| 70% |
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; |
|
| 70% |
With dihydrogen peroxide In water; acetonitrile at 70℃; for 12h; Green chemistry; |
General procedure for selective oxidation of alcohols using cu-nhcpyrmomsmaterials
General procedure: To a 25 mL round bottomed flask equipped with a condenser andmagnetic stir bar was added alcohol (10 mmol), 30% H2O2 (12 mmol,0.37 mL) in CH3CN/ H2O (2/1, 6 mL). Then, Cu-NHCPyrm-OMS(0.5mol%, 0.2 gr) was added to the above solution and the re-sultingmixture was stirred at 70 C for requisite time. The progress of the reactionwas monitored by TLC. After completion of the reaction, themixture was allowed to cool down to the room temperature and thecatalyst was filtrated and washed with ethyl acetate (10 ml) and driedfor next run. The filtrate was concentrated and extracted with mixture ofwater and ethyl acetate. Organic phase was separated, dried overmagnesium sulfate, filtrated through a pad of silica gel, and concentratedwith evaporation under the vacuum to give the correspondingcarbonyl compounds. |
| 64.66% |
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 4h; |
3.1 Step 1. l-phenylpropan-2-one
To a stirred solution of l-phenylpropan-2-ol (10.0 g, 73.42 mmol) in DCM (200 mL) was added DMP (62.3 g, 146.85 mmol) at 0 °C. The resulting mixture was stirred for 4 h at room temperature and then concentrated under reduced pressure. The residue was dissolved in CH2C12 (300 mL). The resulting mixture was filtered, the filter cake was washed with CH2C12 (3 x 50 mL). The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting with 3: 1 ethyl acetate/petroleum ether) to afford l-phenylpropan-2-one as a colorless liquid (6.7 g, 64.6%). 1H- NMR (DMSO-d6, 400 MHz) d (ppm): 7.34-7.30 (m, 2H), 7.26-7.23 (m, 1H), 7.19(d, J = 8 Hz, 2H), 3.76 (s, 2H), 2.13 (s, 3H). LCMS (ES, m/z): 135[M+H]+. |
| 50% |
With tert.-butylhydroperoxide In benzene for 20h; Ambient temperature; |
|
| 50% |
With tert.-butylhydroperoxide; tris(triphenylphosphine)ruthenium(II) chloride for 20h; |
|
| 40% |
With [Pd(N,N'-bis(2,6-(diisopropyl)phenyl)imidazol-2-ylidene)(PCy3)]; oxygen; acetic acid In toluene at 60℃; for 14.5h; Molecular sieve; |
|
| 14% |
With tert.-butylhydroperoxide In methanol at 70℃; for 24h; several conditions investigated and other solvent also investigated; |
|
|
With oxalyl dichloride; dimethyl sulfoxide; triethylamine 1.) dichloromethane, -70 deg C, 15 min; 2.) r.t., 15 min; Multistep reaction; |
|
| 85 % Spectr. |
With 3,3-dimethyldioxirane In acetone at 25℃; |
|
| 66 % Chromat. |
With N-(tert-butyl)benzenesulfinimidoyl chloride; zinc(II) oxide In dichloromethane at 20℃; for 0.5h; |
|
|
With 3,3-dimethyldioxirane In acetone at 0℃; |
|
| 66 % Chromat. |
With N-(tert-butyl)benzenesulfinimidoyl chloride; zinc(II) oxide In dichloromethane at 20℃; for 0.5h; |
|
|
With tert.-butylhydroperoxide; tetrabutyl-ammonium chloride; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 20℃; for 24h; |
|
|
Multi-step reaction with 2 steps
1: 91 percent / CAN; 1-n-butylpyridinium chloroferrate / 0.5 h / 20 °C
2: 92 percent / 1-n-butylpyridinium chloroferrate; pyridinium chlorochromate / 0.58 h / 50 °C |
|
|
Multi-step reaction with 2 steps
1: 91 percent / CAN; 1-n-butylpyridinium chloroferrate / 0.5 h / 20 °C
2: 87 percent / 1-n-butylpyridinium chloroferrate; pyridinium chlorochromate / 0.47 h / 50 °C |
|
| 6 %Chromat. |
With μ-oxo-(tetra-tert-butylphthalocyaninato)iron(III); 2-iodylbenzoic acid 1-methylethyl ester In dichloromethane at 20℃; for 3.5h; |
|
|
Stage #1: 3-phenyl-2-propanol With Jones reagent In acetone at 10℃; for 0.0833333h;
Stage #2: With isopropyl alcohol In acetone |
5.A
1-Phenyl-2-propanol (10 mL, 71 mmol) was dissolved in acetone (800 mL), cooled to 10° C. and Jones reagent was added slowly until an orange color persisted. After 5 min, 2-propanol was added to destroy the excess chromium reagent. The reaction mixture was diluted with Et2O (500 mL) and water (500 mL). The layers were separated and the aqueous layer was extracted once more with Et2O (200 mL). The ether extracts were combined and washed with brine (2*100 mL), dried over MgSO4 and evaporated under reduced pressure. The product was obtained as a yellow oil that was used directly in the next step. |
|
With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water; acetonitrile at 50℃; for 3.5h; |
Typical procedure of oxidation of alcohols with PS-DCIB 2 in CH3CN-H2O:
To a solution of benzyl alcohol 13a (0.021 g, 0.2 mmol) and pyridine (0.052 mL, 0.6mmol) in CH3CN-H2O (2 mL, v/v =1:1) was added PS-DICB 2 (0.223 g, 0.3 mmol) and TEMPO (0.003 g, 0.02 mmol) at room temperature, and the mixture was warmed up to 50 °C and magnetically stirred until the alcohol was consumed (monitored by TLC). The mixture was filtered, and the PS-IB resin was washed with CH3CN (3 x 1 mL) and collected for reuse. To the filtrate was added 2 mL of a standard solution of 2,4-dinitrophenylhydrazine (prepared from 3 g 2,4-DNP, 15 mL concd H2SO4, 70 mL EtOH,and 20 mL H2O). The precipitate was filtered, washed with water and 95% ethanol, dried in vacuum to give 2,4-dinitrophenyl-hydrazone 14a (0.053 g, 92%) |
|
With chromium(VI) oxide; periodic acid In water; acetonitrile at 0 - 5℃; for 1h; |
1
Preparation of l-phenylpropan-2-one (3B): A stock solution of periodic acid/chromium trioxide was prepared according to WO 99/52850 by dissolving periodic acid (11.4 g, 50.0 mmol) and chromium trioxide (23 mg, 1.2 mol %) in wet acetonitrile (0.75% H20) to a volume of 114 mL. This stock solution (104.5 mL) was added to a solution of l-phenylpropan-2-ol (3A) (5.0 g, 36.71 mmol) in wet acetonitrile (150 mL, 0.75% H20) at 0 °C over 1 h, maintaining internal temperature below 5 °C. The reaction was quenched with K2HP04 (11.5 g, 50.5 mmol) in H20 (60 mL).Dichloromethane was added and organic layer separated and washed with brine/H20 (2 x 100 mL), followed by saturated NaHS03/brine. The organic layer was dried(MgS04), filtered and concentrated to give 3B as a yellow oil (5.1 g). 'H-NMR: 300 MHz, (CDC13) δ 7.35-7.10 (m, 5H), 3.65 (s, 2H), 2.11 (s, 3 H). |
| 82 %Spectr. |
With oxygen In 1,4-dioxane at 80℃; for 22h; |
|
| 94 %Spectr. |
With C10H16NO5; potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene at 20℃; for 0.75h; |
|
| 102 mg |
With 4-methyl-morpholine; tetrapropylammonium perruthennate In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere; |
4.1 Production Example 4 Synthesis of Compound 9
(1) 1-Phenyl-2 -propanol (h) (428 mg) was dissolved in dichloromethane (16 mL) , subsequently molecular sieves 4A (400 mg) , N-methylmorpholine (1.10 g) andtetrapropylammonium perruthenate (110 mg) were added thereto and the solution was stirred for 24 hours at room temperature under nitrogen atmosphere. The reaction solution was filtered using a silica gel short column, and the filtrate was dried under reduced pressure and subsequently purified by silica gel chromatography, thereby obtaining ketone (i) (102 mg) . |
|
With dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride In dichloromethane at -20℃; Flow reactor; |
|
|
Multi-step reaction with 2 steps
1: Candida antarctica lipase B / toluene / 20 °C / Enzymatic reaction
2: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / Enzymatic reaction |
|
|
Multi-step reaction with 3 steps
1: Candida antarctica lipase B / toluene / 20 °C / Enzymatic reaction
2: potassium hydroxide; water / methanol
3: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / Enzymatic reaction |
|
| 32 %Chromat. |
With phosphomolybdic acid; oxygen; tetrabutylammonium acetate; palladium diacetate In ethyl acetate at 100℃; for 1h; |
|
| 100 %Spectr. |
With boron trifluoride diethyl etherate; C79H149IO4 In n-heptane at 25℃; for 0.5h; |
General procedure: Typical procedure for oxidationof alcohols using PIB-bound IBX. Thedesired alcohol (0.5 mmol) and 2 equivalents of of PIB-bound IBX were dissolved inheptane. Then 2 equivalents of boron trifluoride diethyl etherate was thenadded into the reaction mixture and the reaction mixture was stirred at roomtemperature for 30 min. Analiquot of the heptane reaction mixture was taken and diluted with CDCl3to determine the conversion of the substrate to product by 1H NMR spectroscopy. Kinetic studies where areaction mixture in CDCl3 was directly analyzed by 1H NMRspectroscopy had previously been used to show that this was a sufficient timefor complete conversion of alcohols to their product aldehyde or ketone Asdescribed above, the products were separated from the heptane solution of anyunreacted or spent oxidant by an extraction with acetonitrile. The heptane from the solution ofpolyisobutylene-bound substrates was then removed at reduced pressure and the PIBspecies isolated were reoxidized as described above. The reoxidized PIB-boundIBX was always characterized by 1H NMR and the ratio of PIB-boundIBX to the ester of PIB-bound 2-iodobenzoic acid was always calculated before asubsequent cycle. |
|
With oxygen In toluene at 100℃; for 0.166667h; |
2.3. Typical Procedure for Alcohol Oxidation.
General procedure: Liquid-phaseoxidation of 1-phenylethanol was performed in glass flaskequipped with a magnetic stirrer, reflux condenser, andthermometer. In a typical experiment, a mixture of the1-phenylethanol (2mmol), toluene (10 mL), and the catalyst(0.3 g) was transferred in a glass three-necked roundbottomedflask (100 mL); the resulting mixture was thenheated to desired temperature with vigorous stirring. Theoxidation experiment was started by bubbling oxygen gas ata flow rate of 20 mL/min into the reaction mixture. After thereaction, the solid catalyst was filtered off by centrifugationand the liquid productswere analyzed by gas chromatographyto determine the conversion of the alcohol and productselectivity by GC, 7890A,Agilent Technologies Inc., equippedwith a flame ionization detector (FID) and a 19019S-001 HPPONAcolumn. |
|
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 2h; |
11.1 Step 1: Preparation of 1 -Phenyl -propan-2-one:
To a stirred solution of 3-Phenyl-2-propanol (5 g, 36.76 mmol) in DCM (70 ml) was added Dess- Martin periodinane (18.7 g, 44.11 mmol) portion wise at about 0°C. The reaction mixture was allowed to stir at room temperature for about 2 hours. After completion of reaction, solvent was evaporated under reduced pressure and 10% EtOAc/n-hexanes was added to the reaction mass. The precipitate obtained was filtered off and washed with 10% EtOAc/n-hexane (3 x 25 mL).The filtrate was concentrated; water (50 mL) was added and extracted with ethyl acetate (3 x 50 ml). The combined organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to give the pure product desired compound (4.5 g, 91.46% yield) as pale yellow liquid which was used in the next step without further purification. |
| 102 mg |
With 4-methyl-morpholine; tetrapropylammonium perruthennate In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere; |
4.1
1-Phenyl-2-propanol (h) (428 mg) was dissolved in dichloromethane (16 mL), subsequently molecular sieves 4 A (400 mg), N-methylmorpholine (1.10 g) and tetrapropylammonium perruthenate (110 mg) were added thereto and the solution was stirred for 24 hours at room temperature under nitrogen atmosphere. The reaction solution was filtered using a silica gel short column, and the filtrate was dried under reduced pressure and subsequently purified by silica gel chromatography, thereby obtaining ketone (i) (102 mg). |
|
With NADP In acetone at 50℃; for 22h; |
|
|
With sodium hypochlorite; potassium dihydrogenphosphate; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl In acetonitrile at 5℃; for 1.5h; |
|
| 87 %Chromat. |
With sodium hypochlorite; (Et4N)2[FeIII(Cl)(biuret-TAML)] In aq. phosphate buffer; acetonitrile at 20℃; for 6h; chemoselective reaction; |
3.1.1. Procedure for reactions at pH 7
General procedure: To a reaction vial containing a magnetic stir bar, unsubstituted Fe-bTAML catalyst, 1 (0.2-0.8mM, 0.5-2mol %), substrate (40mM, 0.04mmol, 1.0equiv.) and pH 7 phosphate buffer (100mM, 300μL aqueous solution) in 700μL acetonitrile were added. An aqueous solution of sodium hypochlorite (2equiv.) was added via syringe pump with continuous stirring over a period of 2-6h at room temperature. The reaction was monitored by TLC and GC. After completion of the reaction, the solvent (CH3CN) was removed under reduced pressure. Saturated aqueous solution of sodium bicarbonate was added to the residual portion and extracted with dichloromethane (2times). The organic part was dried with anhydrous sodium sulphate, analysed by GC-MS to estimate the product GC yield. |
|
With pyridinium chlorochromate In dichloromethane at 20℃; for 24h; Inert atmosphere; |
|
|
With oxygen at 100℃; for 0.233333h; Green chemistry; |
|
|
With nicotinamide adenine dinucleotide phosphate; secondary alcohol dehydrogenase W110G mutant from thermoanaerobacter pseudoethanolicus; acetone In aq. buffer at 50℃; for 24h; Enzymatic reaction; |
|
|
With dihydrogen peroxide; C11H18Br2FeN4(1+)*Br(1-) In acetonitrile at 30℃; for 24h; |
|
|
With NAD; alcohol dehydrogenase from Candida parapsilosis-W286A mutant; Bacillus megaterium ω-transaminase In aq. acetate buffer at 30℃; for 21h; Green chemistry; Enzymatic reaction; |
|
|
With dihydrogen peroxide; 2C14H25N4O2P*Cu(1+)*Cl(1-) In acetonitrile at 78℃; for 4h; Green chemistry; |
2.4. Catalytic reaction
General procedure: Catalytic oxidation of alcohols and sulfides to corresponding acids and sulfoxides bythe synthesized copper complex was investigated in the presence of H2O2 (28 w%) asoxidant. For each run, a suitable amount of 1 as catalyst (5-15 mol%), the substrate(1 mmol), and H2O2 (28 wt%) were reacted in solvent (2 ml). The reactions were performedwith different solvents, temperatures, and molar ratio of substrate to oxidantto get to optimal conditions. The oxidation reactions of sulfides were done at ambienttemperature. The reactions were monitored by thin layer chromatography. At the endof the reactions, the catalyst was separated, washed with acetone, and dried in a vacuumdesiccator to reuse and test the recycling capability. |
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