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CAS No. : | 22204-53-1 | MDL No. : | MFCD00010500 |
Formula : | C14H14O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 230.26 g/mol | Pubchem ID : | - |
Synonyms : |
1. Naproxen |
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.21 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 66.79 |
TPSA : | 46.53 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.33 cm/s |
Log Po/w (iLOGP) : | 1.95 |
Log Po/w (XLOGP3) : | 3.34 |
Log Po/w (WLOGP) : | 3.04 |
Log Po/w (MLOGP) : | 2.57 |
Log Po/w (SILICOS-IT) : | 2.9 |
Consensus Log Po/w : | 2.76 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.61 |
Solubility : | 0.0566 mg/ml ; 0.000246 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.99 |
Solubility : | 0.0233 mg/ml ; 0.000101 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.02 |
Solubility : | 0.0221 mg/ml ; 0.0000962 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.85 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P201-P202-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P308+P313-P332+P313-P337+P313-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335-H361 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Thermotoga maritima esterase Tm1160; In aq. acetate buffer; at 70℃;pH 5.5;Enzymatic reaction; | General procedure: Enzymatic reactions were carried out at 70 C in 1 ml of a reaction mixture containing the purified enzyme (0.235 mg) and 25 mg of racemic ketoprofen ethyl ester dissolved in 50 mM sodium acetate buffer (pH 5.5). The reaction mixture was stirred at 200 rpm. The resulting solution was analyzed by HPLC using the chiral column (25 cm × 4.6 cm, Daical Chemical Industries, Tokyo, Japan). Samples were eluted with n-hexane:2-propanol:acetic acid (90:10:0.5, v/v/v) at a flow rate of 1.0 mL/min and detected at 254 nm. The retention times of racemic ketoprofen ethyl ester, R-ketoprofen, and S-ketoprofen were detected at 5.4, 14.8 and 18.2 min, respectively. The enantioselectivity of the enzyme was calculated with E = ln[1 - c(1 + eep)]/ln[1 - c(1 - eep)], where c and eep represent the degree of conversion and the enantiomeric excess of product, respectively [34]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With C70H72IrO4P2(1+)*BF4(1-); hydrogen; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; under 3750.38 Torr; for 16h;Autoclave; | General procedure: The diastereomeric ratio of the used catalysts was determined by NMR prior to the catalysis. All catalysts and small amounts of liquids were added to the reaction mixture by means of stock solutions. All stock solutions were prepared using anhydrous, degassed solvents. In general, the hydrogenation reactions were carried out using anhydrous, degassed solvents. The catalyst solution, the substrate and, if applicable, the additive were solved in a Schlenk flask in the same solvent used for the stock solutions. A stainless steel autoclave loaded with a NMR tube and a small stirring bar was evacuated and flushed with argon three times before the reaction mixture was transferred into the NMR tube. As soon as the hydrogen gas line was purged with hydrogen gas at least seven times, the autoclave was pressurized with hydrogen gas. After the indicated period of time, the hydrogen gas was discharged from the autoclave. The conversion of the reaction was determined by NMR and the enantiomeric ratio of the product by enantioselective HPLC analysis. | |
With C72H64IrO6P2(1+)*BF4(1-); hydrogen; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; under 3750.38 Torr; for 16h;Autoclave; | General procedure: The diastereomeric ratio of the used catalysts was determined by NMR prior to the catalysis. All catalysts and small amounts of liquids were added to the reaction mixture by means of stock solutions. All stock solutions were prepared using anhydrous, degassed solvents. In general, the hydrogenation reactions were carried out using anhydrous, degassed solvents. The catalyst solution, the substrate and, if applicable, the additive were solved in a Schlenk flask in the same solvent used for the stock solutions. A stainless steel autoclave loaded with a NMR tube and a small stirring bar was evacuated and flushed with argon three times before the reaction mixture was transferred into the NMR tube. As soon as the hydrogen gas line was purged with hydrogen gas at least seven times, the autoclave was pressurized with hydrogen gas. After the indicated period of time, the hydrogen gas was discharged from the autoclave. The conversion of the reaction was determined by NMR and the enantiomeric ratio of the product by enantioselective HPLC analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium acetate;Resolution of racemate;Purification / work up; | Enantiomers of test racemates TR 19-23, of known drugs from the non-steroidal antiinflammatory group, were separated on analytical HPLC columns (250 mm x 4,6 mm), filled with CSP-4 or CSP-3. Since these compounds are structurally free carboxyl acids, it was necessary to use a polar mobile phase containing a certain amount of ammonium acetate. Results obtained by the enantioselective separation of these compounds are shown in Table 5 and the chromatogram achieved for the enantiomers of naproxen is shown in Figure 8. <n="20"/>TABLE 5 Enantiomer separations for test racemate TR 20-23 on the column filled withCSP-3 (250 mm x 4.6 mm ID), with hexane : 2-PrOH = 8:2 + lg/L NH4OAc as the mobile phase, 1 ml/min, 254 nm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; | 39a. 2-(4-(2-Hydroxyethoxy)phenoxy)ethyl (2S)-2-(6-methoxy(2-naphthyl))propanoate A solution of (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (naproxen, 4.27 g, 18.5 mmol), hydroquinone bis(2-hydroxyethyl) ether (10.6 g, 53.3 mmol), N,N-dimethylaminopyridine (DMAP, 2.71 g, 22.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (9.34 g, 48.7 mmol) and NEt3 (13 mL, 93.3 mmol) in DMF (100 mL) was stirred at ambient temperature overnight. The reaction mixture was evaporated to dryness under vacuum and the residue was partitioned between HCl (3N, 100 mL) and CH2Cl2 (200 mL). The organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated. The product was separated by silica gel column chromatography eluding with EtOAc/hexane (1:1, Rf=0.15) and then recrystallized from ethyl ether and hexane to give the title compound as a white solid (6.01 g, 31% yield). Mp 76-78 C. 1H NMR (CDCl3) delta 7.7-7.64 (m, 3H), 7.42-7.38 (m, 1H), 7.15-7.08 (m, 2H), 6.74-6.72 (m 4H), 4.45-4.36 (m, 2H), 4.1-3.85 (m, 7H), 3.90 (s, 3H), 2.13 (br. t, 1H), 1.58 (d, J=7.2 Hz, 3H). 13C NMR (CDCl3) delta 174.6, 157.5, 153.0, 152.8, 135.4, 133.6, 129.2, 128.8, 127.1, 126.1, 125.9, 118.8, 115.7, 115.3, 105.5, 69.7, 66.6, 63.1, 61.4, 55.2, 45.2, 18.4. MS(API) m/z 428 (M+NH4)+. Anal. calcd. for C24H26O6: C, 70.23; H, 6.38. Found: C, 70.01; H, 6.39. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzoic acid anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 6h;Resolution of racemate;Product distribution / selectivity; | Experimental Example 8Production of Optically Active Ester and Optically Active Carboxylic Acid Using Naproxen (Optical Resolution of Naproxen) As shown by the above reaction equation, an optically active ester and optically active carboxylic acid are obtained by reacting 1,1-di(1-naphthyl)methanol or 1,1-di(9-phenanthryl)methanol and racemic naproxen. The results are shown in Table 8.; Entry 53(R)-naproxen di(1-naphthyl)methylesterHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/9, flow rate=1.0 mL/ml): tR=13.7 min (10.6%), tR=17.4 min (89.4%);IR (neat): 3034, 1733, 1604, 1508, 782, 679 cm-1;1H NMR (CDCl3): delta8.29 (s, 1H, 1'-H), 8.00-7.90 (m, 1H, Ph), 7.82-6.96 (m, 17H, Ph), 6.95-6.81 (m, 2H, Ph), 3.86 (q, J=7.0 Hz, 1H, 2-H), 3.79 (s, 3H, OMe), 1.49 (d, J=7.0 Hz, 3H, 3-H);13C NMR (CDCl3): delta173.6, 157.6, 135.1, 134.7, 134.5, 133.8, 133.7, 133.6, 131.2, 130.8, 129.3, 129.1, 128.9, 128.8, 128.7, 128.6, 128.3, 127.1, 126.7, 126.5, 126.3, 126.2, 125.8, 125.6, 125.3, 125.2, 125.0, 123.4, 123.3, 118.9, 105.5, 71.2, 55.2, 45.5, 18.3;HR MS: calculated for C35H28O3Na (M+Na+)=519.1931; found 519.1932. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzoic acid anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 6h;Resolution of racemate;Product distribution / selectivity; | Entry 55To a dichloromethane solution (2.0 mL) containing benzoic anhydride (54.3 mg, 0.240 mmol) and racemic naproxen (46.1 mg, 0.200 mmol); diisopropylethylamine (62.7 muL, 0.360 mmol), benzotetramisole (2.5 mg, 0.010 mmol), and 1,1-di(9-phenanthryl)methanol (38.4 mg, 0.100 mmol) were added in order at room temperature. After stirring the reaction mixture solution at room temperature for 6 hr, the reaction was stopped with saturated ammonium chloride water. After fractionating the organic layer, the aqueous layer was extracted 4 times with dichloromethane. After combining the organic layers, they were dried with anhydrous sodium sulfate. After filtering the solution, it was vacuum concentrated, and the obtained mixture was fractionated by thin layer silica gel chromatography to obtain the corresponding optically active naproxen ester (59.7 mg, 50%, 88% ee) and the unreacted optically active naproxen (12.6 mg, 27%, 61% ee).(R)-naproxen di(9-phenanthryl)methylesterHPLC (CHIRALCELL OD-H, i-PrOH/hexane=1/4, flow rate=0.75 mL/mi): tR=23.7 min (94.1%), tR=41.1 min (5.9%);IR (KBr): 3063, 1731, 1605, 1265, 1028, 749, 727 cm-1;1H NMR (CDCl3): delta8.84-8.50 (m, 4H, Ph), 8.43 (s, 1H, 1'-H), 8.25-8.12 (m, 1H, Ph), 7.80-7.08 (m, 18H, Ph), 6.83-6.75 (m, 1H, Ph), 4.03 (q, J=7.1 Hz, 1H, 2-H), 3.96 (s, 3H, OMe), 1.64 (d, J=7.1 Hz, 3H, 3-H);13C NMR (CDCl3): delta173.5, 157.9, 135.2, 134.0, 132.9, 132.6, 131.0, 130.9, 130.6, 130.6, 130.3, 130.2, 129.8, 129.5, 129.1, 129.0, 128.9, 128.3, 128.0, 127.4, 127.3, 127.2, 126.8, 126.6, 126.6, 126.5, 126.4, 126.3, 126.2, 124.2, 123.9, 123.4, 123.1, 122.4, 122.2, 119.0, 105.6, 71.0, 55.4, 45.7, 18.0.(S)-naproxenHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/10/0.01, flow rate=1.0 mL/min); tR=13.8 min (18.9%), tR=15.8 min (81.1%);1H NMR (CDCl3): delta9.42 (br s, 1H, COOH), 7.68-7.55 (m, 3H, Ph), 7.33-7.28 (m, 1H, Ph), 7.13-6.99 (m, 2H, Ph), 3.83 (s, 3H, OMe), 3.79 (q, J=7.2 Hz, 1H, 2-H), 1.50 (d, J=7.2 Hz, 3H, 3-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 30℃;Product distribution / selectivity; | Racemic (+/-)-10, 11 -dihydro-10-hydroxy-5H- dibenz[b,f]azepine-5-carboxamide (100 g), dichloromethane (500 mL) and naproxen (108.69 g) are charged into a round-bottom flask and stirred for 5 minutes. Dicyclohexylcarbodiimide ("DCC", 105.7 g) and 1-hydroxybenzotriazole (OmicronBetaTau, 5.5 g) are added to the mixture. The reaction mixture is maintained at 30C for 7-8 hours, then filtered and the solid washed with dichloromethane (300 mL). The filtrate is evaporated completely under reduced pressure. Ethyl acetate (1800 mL) is added to the mass and stirred at 29C for 15-20 minutes. The mixture is heated to reflux temperature and maintained for 50-60 minutes. The solid obtained is collected by filtration, washed with ethyl acetate (360 mL) and dried at 70C to afford 24.9 g of naproxen ester of (S)-(+)-10, 1 1-dihydro-10- hydroxy-5H-dibenz[b,f]azepine-5-carboxamide. Purity by HPLC: 91.8%; choral purity by HPLC: 93.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With esterase from Sulfolobus tokodaii strain 7; In acetonitrile; at 70℃;pH 7;Enzymatic reaction; | General procedure: Two hundred microliters of 50 mM substrate (1a or 1b) solution in CH3CN was added to 4 ml of 400 mM HEPES-NaOH buffer (pH 7). To the resulting solution, 1 ml of Est007 solution (25 mug/ml) was added and the mixture was stirred for 48 h at 70 C. The reaction was stopped by addition of 2 ml of 2 M HCl. The products were extracted with 5 ml diisopropyl ether. The organic layer (4 ml) was concentrated in vacuo, and to this was added 400 mul diisopropyl ether, 100 mul methanol, and an excess amount of Me3SiMeN2 in hexane. The solution was vortexed and allowed to stand at room temperature for 30 min. Enatiomeric excess of methyl ester of 5a and 5b was determined by HPLC analysis using CHRALCEL OJ (Daicel Corporation, Japan). To determine the conversion rate, 500 mul of the reaction mixture was transferred to the tube, and the reaction was stopped by addition of 200 mul of CH3CN containing 2% CF3CO2H. The products were extracted with EtOAc which contains diethyl phthalate as an internal standard. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 14h;Inert atmosphere; | To a solution of naproxen (115 mg, 0.50 mmol) in anhydrous DMF (5 mL) was added the above-prepared compound (114 mg, 0.6 mmol), HBTU (247 mg, 0.65 mmol) and diisopropylethylamine (130 muL, 0.75 mmol). The mixture was stirred at room temperature under argon for 14 h, and then concentrated under reduced pressure. The residue was diluted with EtOAc and washed with 1 M HCl(aq), saturated NaHCO3(aq), and brine. The organic phase was dried over MgSO4, filtered, and purified by silica gel chromatography (EtOAc/hexane=1:9) to afford the desired product 60 (169 mg, 84%). C21H26N2O4S; colorless oil; 1H NMR (CDCl3, 400 MHz) delta 12.31 (0.55 H, s), 12.19 (0.45 H, s), 7.69 (3H, m), 7.38 (1H, br), 7.15-7.07 (2H, m), 4.02-3.90 (1H, br), 3.87 (3H, s), 2.30 (3H, s), 1.62 (3H, d, J=6.8 Hz), 1.37 (9H, br); HRMS (ESI) calcd for C21H27N2O4S: 403.1692, found: m/z 403.1700 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The compounds were synthesized by solid phase peptide synthesis (SPPS) using 2-chlorotrityl chloride resin. The corresponding N-Fmoc protected amino acids with side chains properly protected, Fmoc-succinated cystamine, and <strong>[175281-76-2]4-(4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy)butanoic acid</strong> were used for SPPS. The first amino acidwas loaded on the resin at the C-terminal with the loading efficiency about 0.6 mmol/g. 20% piperidine in anhydrous N,N-dimethylformamide (DMF) was used during deprotection of Fmoc group. The next Fmoc-protected amino acid (3 equiv.) was then coupled to the free amino group using O-(Benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate (HBTU, 1 equiv.to Fmoc-AA) as the coupling reagent. The growth of the peptide chain was according to the established Fmoc SPPS protocol. After the last coupling step, excessive reagents were removed by a single DMF wash for 5minutes (5 mL per gram of resin), followed by five steps of washing using DCM for 1 min (5 mL per gram of resin). The peptide derivative was cleaved using 92.5% of trifluoroacetic acid with 2.5% of TMS, 2.5% of phenol,and 2.5% of H2O for 20 minutes. 20 mL per gram of resin of ice-cold diethylether was then added to cleavage reagent. The resulting precipitate was filtrated and washed by ice-cold diethylether. The resulting solid was purified by HPLC and dried by lyophilizer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The compounds were synthesized by solid phase peptide synthesis (SPPS) using 2-chlorotrityl chloride resin. The corresponding N-Fmoc protected amino acids with side chains properly protected, Fmoc-succinated cystamine, and <strong>[175281-76-2]4-(4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy)butanoic acid</strong> were used for SPPS. The first amino acidwas loaded on the resin at the C-terminal with the loading efficiency about 0.6 mmol/g. 20% piperidine in anhydrous N,N-dimethylformamide (DMF) was used during deprotection of Fmoc group. The next Fmoc-protected amino acid (3 equiv.) was then coupled to the free amino group using O-(Benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate (HBTU, 1 equiv.to Fmoc-AA) as the coupling reagent. The growth of the peptide chain was according to the established Fmoc SPPS protocol. After the last coupling step, excessive reagents were removed by a single DMF wash for 5minutes (5 mL per gram of resin), followed by five steps of washing using DCM for 1 min (5 mL per gram of resin). The peptide derivative was cleaved using 92.5% of trifluoroacetic acid with 2.5% of TMS, 2.5% of phenol,and 2.5% of H2O for 20 minutes. 20 mL per gram of resin of ice-cold diethylether was then added to cleavage reagent. The resulting precipitate was filtrated and washed by ice-cold diethylether. The resulting solid was purified by HPLC and dried by lyophilizer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.3% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; for 22.5h;Cooling with ice; Inert atmosphere; | 2-(1H-benzo[d]imidazol-1-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide-HCl (EDC-HCl) (2.20 g, 11.5 mmol) was added solid all at once to a magnetically stirred solution of naproxen (2.30 g, 10.0 mmol), 1-(2-hydroxyethyl)imidazole (1.12 g, 10.0 mmol) and 4-Dimethylaminopyridine (61 mg, 0.5 mmol) in dry tetrahydrofuran (50 mL) cooled in an ice bath and kept under nitrogen. The reaction mixture was stirred in an ice bath for 30 min and at ambient temperature. More EDC-HCl (400 mg, 2 mmol) was added after 13 hrs, 17 hrs. After stirring for 22 hrs at room temperature the mixture was concentrated and the residue partitioned between water (50 mL), saturated NH4Cl (20 mL) and EtOAc (120 mL). The organic layer was washed with 50% saturated NH4Cl (2*50 mL), 50% saturated NaHCO3 (50 mL) and brine (50 mL). The organic layer was dried and concentrated. The oily residue was purified by Flash Chromatography using ethyl acetate and heptanes as eluent afforded a colourless oil (2.74 g, 84%) after drying in high vacuum. The oil was crystallised from ether and recrystallised from Tert-butylmethylether (?20 mL, seeded) to afford the title compound as a colourless solid (2.21 g, 68.3%). Mp. 60.6-61.3 C. 1H NMR (400 MHz, DMSO) delta 7.80 (d, J=9.0 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.68 (d, J=1 Hz, 1H), 7.51 (s, 1H), 7.33 (dt, J=5.5, 3 Hz, 1H), 7.30 (d, J=2.5 Hz, 1H), 7.17 (dd, J=9, 2.5 Hz, 1H), 6.98 (t, J=1 Hz, 1H), 6.78 (t, J=1 Hz, 1H), 4.34-4.12 (m, 4H), 3.92 (q, J=7 Hz, 1H), 3.88 (s, 3H), 1.45 (d, J=7 Hz, 3H). 13C NMR (101 MHz, DMSO) delta 173.52, 157.19, 137.40, 135.30, 133.33, 129.15, 128.37, 128.25, 126.99, 126.20, 125.63, 119.46, 118.73, 105.69, 63.74, 55.15, 44.94, 44.35, 18.19. |
68.3% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; for 42.5h;Cooling with ice; Irradiation; | 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide-HCI (EDC-HCI) (2.20 g, 1 1.5 mmol) was added solid all at once to a magnetically stirred solution of naproxen (2.30 g, 10.0 mmol), 1-(2-hydroxyethyl)imidazole (1 .12 g, 10.0 mmol) and 4- Dimethylaminopyridine (61 mg, 0.5 mmol) in dry tetrahydrofuran (50 ml.) cooled in an ice bath and kept under nitrogen. The reaction mixture was stirred in an ice bath for 30 min and at ambient temperature. More EDC-HCI (400 mg, 2 mmol) was added after 13 hrs, 17 hrs . After stirring for 22 hrs at room temperature the mixture was concentrated and the residue partitioned between water (50 ml_), saturated NH4CI (20 ml.) and EtOAc (120 ml_). The organic layer was washed with 50 % saturated NH4CI (2 x 50 ml_), 50 % saturated NaHC03 (50 ml.) and brine (50 ml_). The organic layer was dried and concentrated. The oily residue was purified by Flash Chromatography using ethyl acetate and heptanes as eluent afforded a colourless oil (2.74 g, 84 %) after drying in high vacuum. The oil was crystallised from ether and recrystallised from Tert-butylmethylether (-20 ml_, seeded) to afford the title compound as a colourless solid (2.21 g, 68.3 %). Mp. 60.6-61.3 C. 1H NMR (400 MHz, DMSO) delta 7.80 (d, J = 9.0 Hz, 1 H), 7.77 (d, J = 8.5 Hz, 1 H), 7.68 (d, J = 1 Hz, 1 H), 7.51 (s, 1 H), 7.33 (dt, J = 5.5, 3 Hz, 1 H), 7.30 (d, J = 2.5 Hz, 1 H), 7.17 (dd, J = 9, 2.5 Hz, 1 H), 6.98 (t, J = 1 Hz, 1 H), 6.78 (t, J = 1 Hz, 1 H), 4.34 - 4.12 (m, 4H), 3.92 (q, J = 7 Hz, 1 H), 3.88 (s, 3H), 1 .45 (d, J = 7 Hz, 3H). 13C NMR (101 MHz, DMS0) 5 173.52, 157.19, 137.40, 135.30, 133.33, 129.15, 128.37, 128.25, 126.99, 126.20, 125.63, 1 19.46, 1 18.73, 105.69, 63.74, 55.15, 44.94, 44.35, 18.19. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Yarrowia lipolytica Lip2p lipase; In decane; at 20℃; for 100h;Enzymatic reaction;Kinetics; | General procedure: In a 2 mL reactor (Eppendorf), 750 lL of culture supernatant (or the concentrate supernatant) containing the enzyme and 750 lL ofracemic ethyl ibuprofen, naproxen or ketoprofen (50 mM indecane) were added. The reactors were stirred in a vortex Genie2 (D. Dutscher, Brumat, France) at room temperature for 100 h.At regular time intervals, the progress of the reaction was monitored by analyzing the organic phase composition after phase separationby centrifugation (dilution 1, 10 and 30 in hexane for the ibuprofen, naproxen and ketoprofen ester, respectively). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | To the solution of (naproxen, 230mg 1.0mmol) in 8mL of acetonitrile, DMAP (18mg, 0.15mmol) and EDCI (190mg, 1.0mmol) were added with stirring at room temperature for 0.5h. To the reaction mixture <strong>[25984-63-8]4-hydroxythiobenzamide</strong> (153mg, 1.0mmol) was added and stirred for 4hat room temperature. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent. The oily residue thus obtained was dissolved in trichloromethane; the organic layer was washed with brine, with NaCl 5%, and then dried on anhydrous Na2SO4, filtered and the solvent evaporated. The crude product was chromatographed on a silica gel (CHCl3/CH3OH 30:1), and 148.8mg pale yellow solid was obtained. Yield: 42.0%. IR (KBr, cm-1): 3398 (w, NH2), 3298 (w, NH2), 1755 (v, COO), 1214 (s, COC), 1170 (v, C=S). 1H NMR (DMSO-d6, TMS, ppm): delta 1.59 (d, J=7.2Hz, 3H, Ar-C-CH3), 3.88 (s, 3H, O-CH3), 4.25 (q, J=7.2Hz, 1H, Ar-CH), 7.09 (d, J=8.8Hz, 2H, Ar-H), 7.18 (dd, J=8.8Hz, 2.4Hz, 1H, Ar-H), 7.33 (s, 1H, Ar-H), 7.52 (d, J=8.4Hz, 1H, Ar-H), 7.85 (d, J=4.4Hz, 2H, Ar-H), 7.87 (s, 1H, Ar-H), 7.90 (d, J=8.4Hz, 2H, Ar-H), 9.53 (s, 1H, NH), 9.91 (s, 1H, NH). 13C NMR (DMSO-d6, TMS, ppm): delta18.9, 45.0, 55.7, 106.3, 119.4, 121.5, 126.4, 126.7, 127.8, 129.0, 129.3, 129.7, 133.9, 135.6, 153.2, 157.8, 173.1. ESI-HRMS (m/z): calcd. for C21H19NO3SNa [M+Na]+: 388.0983; found 388.0979. |
Tags: 22204-53-1 synthesis path| 22204-53-1 SDS| 22204-53-1 COA| 22204-53-1 purity| 22204-53-1 application| 22204-53-1 NMR| 22204-53-1 COA| 22204-53-1 structure
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Code | Phrase |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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