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[ CAS No. 51146-57-7 ] {[proInfo.proName]}

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Chemical Structure| 51146-57-7
Chemical Structure| 51146-57-7
Structure of 51146-57-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 51146-57-7 ]

CAS No. :51146-57-7 MDL No. :MFCD00069290
Formula : C13H18O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HEFNNWSXXWATRW-SNVBAGLBSA-N
M.W : 206.28 Pubchem ID :114864
Synonyms :
(-)-Ibuprofen;(R)-Ibuprofen;Levibuprofen;l-Ibuprofen

Calculated chemistry of [ 51146-57-7 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.18
TPSA : 37.3 Ų

Pharmacokinetics

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) : -5.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.21
Log Po/w (XLOGP3) : 3.5
Log Po/w (WLOGP) : 3.07
Log Po/w (MLOGP) : 3.13
Log Po/w (SILICOS-IT) : 3.15
Consensus Log Po/w : 3.01

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.36
Solubility : 0.0909 mg/ml ; 0.000441 mol/l
Class : Soluble
Log S (Ali) : -3.97
Solubility : 0.0223 mg/ml ; 0.000108 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.44
Solubility : 0.0749 mg/ml ; 0.000363 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 51146-57-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P260-P264-P270-P271-P280-P304+P340-P305+P351+P338-P312-P330-P403+P233-P501 UN#:N/A
Hazard Statements:H302-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51146-57-7 ]

* 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.

  • Downstream synthetic route of [ 51146-57-7 ]

[ 51146-57-7 ] Synthesis Path-Downstream   1~85

  • 1
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YieldReaction ConditionsOperation in experiment
With ammonium acetate; In hexane; isopropyl alcohol;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.
With 2C8H8N5O2(1-)*Cu(2+); In hexane; at 60℃;Resolution of racemate;Catalytic behavior; Prior to analysis, the MOFs having repeating units of (SS)-(IA1) of the invention was prepared from the MOFs having repeating units of (SS)-(IBI ') by activation. Particularly, MOFs having repeating units of (SS)-(IBI ') was activated in vacuum at 150C for 12 h on a Schlenk line. 30 mg of the activated MOF having repeating units of (SS)-(IA1) was placed into a solvent as defined in Table 8 at the appropriate temperature as shown in Table 8 with racemic ibuprofen (50% S/R) in a molar ratio (SS)- (IA1):ibuprofen of 1 :3. The reaction was stirred at the temperature indicated in Table 8 overnight. The reaction was filtered to remove the solid, which was washed with a small amount of fresh acetonitrile to remove any ibuprofen sorbed on the surface of the framework. The term "mother liquor" refers to the mixture of the filtrate and the first wash. he amount and chirality of ibuprofen sorbed by the activated MOF was extracted from the solid by suspension in CHCI3 (2 ml) at room temperature for 1 hour. After this time the solid was removed by filtration and the filtrate was analysed by 1H NMR. The enantiomeric excess was determined comparing with the commercially available pure enantiomer, (S)- (+)-lbuprofen or (S)-(+)-4-lsobutyl-a-methylphenylacetic acid, or (S)-(+)-2-(4-lsobutylphenyl)propionic acid (CAS: 51146-56-6, Sigma-Aldrich); and (R)-(+)-lbuprofen or (R)-(+)-4-lsobutyl-a-methylphenylacetic acid or (R)-(+)-2-(4-lsobutylphenyl)propionic acid (CAS: 51146-57-7, Santa Cruz Bio Biotech) using a ultra- performance convergence chromatography (UPPC), ACQUITY UPC2 Waters system with Diode Array Detector; a Column: ChiralPak IA 4.6mm x 100mm, 3mueta, under the following conditions: CO2/ACN/TFA 88:12:0.5, 3ml/min, 1500 psi. Table 8 summarizes the amount of each one of the enantiomer of ibuprofen in the mother liquor and also in the ibuprofen extracted from the MOFs having repeating units of (SS)-(IA1) of the in the invention. Furthermore, Table 8 also specifies the solvent and the temperature of each one of the independent runs:
With colistin sulfate-based polymer monolithic column; In methanol; water; at 20℃;Resolution of racemate; Green chemistry; General procedure: The colistin sulfate-based polymer monolithic capillary column was prepared as describedabove and investigated for the nano-LC enantioseparation of a set of different classes of racemicpharmaceuticals, namely: beta-blockers, alpha-blockers, anti-inflammatory drugs, antifungal drugs,norepinephrine-dopamine reuptake inhibitors, catecholamines, sedative hypnotics, antihistamines,antibacterial drugs, anticancer drugs and antiarrhythmic drugs. Although reversed phaseenantio-selective LC examples are limited, macrocyclic antibiotics were previously used inenantioseparation chromatography under reversed phase chromatographic mode [34,36-38,42-45].The initial mobile phase selected for the enantioseparation separation of racemates 1-37 (Figure 3) wasa binary mixture of methanol/water screened from 95:5 to 5:95 nu/nu at 1 mL/min flow rate at fixed UVdetection 219 nm with eleven compounds separated (Rs 1) (Table 1). For examples, in MeOH/H2O80:20 nu/nu, only ibuprofen (7) was separated, while in MeOH/H2O 40:60, indoprofen (10), hexaconazole(15) and miconazole (16) were separated. In MeOH/H2O 10:90 nu/nu, aminoglutethimide (22), tyrosine(29) and O-methoxymandelic acid (34) were also separated. The addition of an additive, namelytriethylamine (TEA) 1% nu/nu in 10:90, resulted in the separation of acebutolol (4) normetanephrine(21), propafenone (26), tyrosine (29) and 4-hydroxy-3-methoxymandelic acid (35) (Figure 4), whilenon-acceptable separations were achieved by addition of the acidic additive namely trifluoroaceticacid (TFA). In an attempt to use normal phase namely n-hexane/2-propanol mixture ranging from10-90% (nu/nu) resulted in resolution less than 1. All chromatographic data are summarized in Table 1.
  • 5
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  • 6
  • [ 2627-86-3 ]
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  • (R)-2-(4-Isobutyl-phenyl)-N-((S)-1-phenyl-ethyl)-propionamide [ No CAS ]
  • 8
  • [ 51146-57-7 ]
  • [ 81576-57-0 ]
  • 9
  • [ 121839-78-9 ]
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  • 10
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  • 11
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  • 17
  • [ 123054-51-3 ]
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  • 18
  • (2R,3R)-2,3-Bis-[2-(4-isobutyl-phenyl)-propionyloxy]-succinic acid diethyl ester [ No CAS ]
  • [ 51146-56-6 ]
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  • 19
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  • 25
  • [ 123054-47-7 ]
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  • 26
  • [ 105538-90-7 ]
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  • 27
  • [ 85277-56-1 ]
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  • 28
  • [ 93673-08-6 ]
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  • (S)-3-(4'-Isobutylphenyl)butanoic acid [ No CAS ]
  • (S)-4-(4'-Isobutylphenyl)pentanoic acid [ No CAS ]
  • 29
  • [ 5674-02-2 ]
  • [ 76099-91-7 ]
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  • 30
  • (3S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl α-<4-(2-methylpropyl)phenyl>propionate [ No CAS ]
  • [ 51146-56-6 ]
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  • 31
  • (3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl α-<4-(2-methylpropyl)phenyl>propionate [ No CAS ]
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  • 32
  • [ 6448-14-2 ]
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YieldReaction ConditionsOperation in experiment
96% In the glove box, the catalyst [(Sa-DTB-SIPHOX)Ir(COD)]BARF 4 (4.7 mg, 0.0025 mmol) and 2 - (4 - isobutyl-phenyl) acrylic acid 5 (102 mg, 0.5 mmol) are weighted in the reaction inner tube with stirring bar, then the reaction inner tube is sealed for use. When the reaction inner tube is took out, triethylamine (25 mg, 0.25 mmol) and anhydrous methanol (2 mL) are added with a syringe, then the inner tube is placed into the hydrogenation reactor, the mixture is stirred at room temperature under the hydrogen pressure of 0.6 Mpa to react for 24 h. Then the stirring is stopped, the hydrogen is released. After the system is condensed by evaporating off rotatably, the system is adjusted pH <3 with 3N hydrochloric acid water solution, extracted with diethyl ether (10 mL .x. 3), and separated, the organic phase is collected, washed with saturated salt water, and dried with anhydrous sodium sulfate. The desiccant is removed by suction filtration, the solvent is evaporated off by rotating, then the object product 6 is obtained, and is a white solid, through the 1H NMR analysis, the conversion rate is 100percent and the yield is 96percent. Mp 53-55 °C; [alpha]30,D -41.5 (c 2.0, ethanol); 1H NMR (400 MHz, CDCl3): delta 11.27 (brs, 1H, COOH), 7.24 (d, J = 8.4 Hz, 2H, Ar-H), 7.08 (d, J = 7.6 Hz, 2H, Ar-H), 3.68 (q, J = 6.8 Hz, 1H, CH), 2.43 (d, J = 6.8 Hz, 2H, CH2), 1.88-1.78 (m, 1H, CH), 1.48 (d, J = 7.2 Hz, 3H, CH3), 0.88 (d, J = 6.4 Hz, 6H, CH3); after it is converted to methyl ester, its ee value is 90percent through the chiral GC analysis.
With C54H68IrNP(1+)*C32H12BF24(1-); hydrogen; caesium carbonate; In methanol; at 45℃; under 4500.45 Torr; for 0.166667h;Glovebox; Sealed tube; The catalyst (S)-5a (0.9mg, 0.0005mmol) and 2-4-isobutyl-acrylic acid 6a (102mg, 0.5mmol) were weighed from glove box and transferred into the reaction inner tube containing a stir bar. The tube was sealed as a spare. Cesium carbonate (82mg, 0.25mmol) and methanol (2mL) were added into the tube after fetching out the tube. The inner tube was placed in the hydrogenation reaction still. The original atmosphere was displaced with hydrogen atmosphere by inflating-deflating operation (3-5 times). The hydrogen pressure was ultimately set at 0.6MPa. At the temperature of 45 , the reaction was proceeded with stirring until the pressure stopped decreasing. After stopping stirring to release hydrogen and concentrating the system with rotary steaming, the pH value of the system was adjusted with 3 N hydrochloric acid until pH 3). The organic phases merged together were washed by sodium chloride solution and dried by anhydrous sodium sulfate. The drying agent was removed by suction filtration. The target product (R) 7a was obtained after solvent was removed by rotary steaming. The conversion rate was analyzed by 1H NMR and the ee value was analyzed by chiral GC after the product was transformed into corresponding methyl ester. The experimental results determined are listed in Table 2:
With C54H72IrNP(1+)*C32H12BF24(1-); hydrogen; caesium carbonate; In methanol; at 45℃; under 4500.45 Torr; for 0.166667h;Glovebox; Example 6 Asymmetric Hydrogenation of (R)-Isoibuprofen The catalyst (0.0005 mmol) and 2-4-isobutyl-acrylic acid 6a (102 mg, 0.5 mmol) were weighed from glove box and transferred into the reaction inner tube containing a stir bar. The tube was sealed as a spare. Cesium carbonate (82 mg, 0.25 mmol) and methanol (2 mL) were added into the tube after fetching out the tube. The inner tube was placed in the hydrogenation reaction still. The original atmosphere was displaced with hydrogen atmosphere by inflating-deflating operation (3-5 times). The hydrogen pressure was ultimately set at 0.6 MPa. At the temperature of 45, the reaction was proceeded with stirring until the pressure stopped decreasing. After stopping stirring to release hydrogen and concentrating the system with rotary steaming, the pH value of the system was adjusted with 3 N hydrochloric acid until pH<3. The mixture was extracted by ether (10 mL 3). The organic phases merged together were washed by sodium chloride solution and dried by anhydrous sodium sulfate. The drying agent was removed by suction filtration. The target product 7a was obtained after solvent was removed by rotary steaming. Melting point: 53-55. [alpha]D30?52 (c 2.0, ethanol); 1H NMR (400 MHz, CDCl3): delta 9.98 (brs, 1H, COOH), 7.24 (d, J=7.6 Hz, 2H, Ar?H), 7.12 (d, J=7.6 Hz, 2H, Ar?H), 3.73 (q, J=7.2 Hz, 1H, CH), 2.47 (d, J=7.2 Hz, 2H, CH2), 1.86 (septet, J=6.8 Hz, 1H, CH), 1.52 (d, J=7.2 Hz, 3H, CH3), 0.92 (d, J=6.4 Hz, 6H, CH3)} [0067] The conversion rate was analyzed by 1H NMR and the ee value was analyzed by chiral GC after the product was transformed into corresponding methyl ester. The experimental results determined are listed in Table 1:
  • 33
  • (Z)-2-(4-Isobutyl-phenyl)-1-trimethylsilanyloxy-propen-1-ol [ No CAS ]
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  • 34
  • [ 100-02-7 ]
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  • (R)-2-(4-Isobutyl-phenyl)-propionic acid 4-nitro-phenyl ester [ No CAS ]
  • 35
  • [ 127729-01-5 ]
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  • 37
  • [ 152140-57-3 ]
  • isobutylzinc [ No CAS ]
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  • 39
  • [ 50-00-0 ]
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  • [ 93469-76-2 ]
  • 41
  • [ 71381-91-4 ]
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  • 43
  • [ 51146-57-7 ]
  • [ 62173-99-3 ]
  • (R)-2-(4-Isobutyl-phenyl)-propionic acid (S)-carboxy-phenyl-methyl ester [ No CAS ]
  • 44
  • [ 51146-57-7 ]
  • [ 97415-09-3 ]
  • (R)-2-(4-Isobutyl-phenyl)-propionic acid (R)-carboxy-phenyl-methyl ester [ No CAS ]
  • 45
  • 2-(4-isobutylphenyl)-2-methyl-trimethylsilylketene S-methyl thioacetal [ No CAS ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • 46
  • 2-(4-isobutylphenyl)-2-methyl-trimethylsilylketene S-ethyl thioacetal [ No CAS ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • 47
  • 2-(4-isobutylphenyl)-2-methyl-t-butyldimethylsilylketene S-methyl thioacetal [ No CAS ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • 48
  • 2-(4-isobutylphenyl)-2-methyl-t-butyldimethylsilylketene S-ethyl thioacetal [ No CAS ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • 49
  • [ 74-85-1 ]
  • [ 63444-56-4 ]
  • [ 51146-56-6 ]
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  • 50
  • (R)-2-(4-Isobutyl-phenyl)-propionic acid (1R,2S)-1-acetylamino-indan-2-yl ester [ No CAS ]
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  • 51
  • [ 40150-92-3 ]
  • [ 143-33-9 ]
  • [ 38861-78-8 ]
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  • 52
  • [ 462-08-8 ]
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  • 2-(4-isobutyl-phenyl)-<i>N</i>-pyridin-3-yl-propionamide [ No CAS ]
  • 53
  • [ 504-24-5 ]
  • [ 51146-57-7 ]
  • 2-(4-isobutyl-phenyl)-<i>N</i>-pyridin-4-yl-propionamide [ No CAS ]
  • 54
  • [ 504-29-0 ]
  • [ 51146-57-7 ]
  • 2-(4-isobutyl-phenyl)-<i>N</i>-pyridin-2-yl-propionamide [ No CAS ]
  • 55
  • [ 5049-61-6 ]
  • [ 51146-57-7 ]
  • 2-(4-isobutyl-phenyl)-<i>N</i>-pyrazin-2-yl-propionamide [ No CAS ]
  • 56
  • [ 163133-86-6 ]
  • [ 51146-57-7 ]
  • 2-(4-isobutyl-phenyl)-<i>N</i>-pyrimidin-4-yl-propionamide [ No CAS ]
  • 57
  • [ 67-56-1 ]
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  • [ 81576-57-0 ]
  • 58
  • [ 98-10-2 ]
  • [ 51146-57-7 ]
  • (R)-2-(4-isobutylphenyl)-N-(benzenesulfonyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% A 50 ml round bottom flask was charged with CDI (0.41 g, 2.25 mmol) in a dry dichloromethane solution of (R)-2- (4-isobutylphenyl) propionic acid (0. 52 g, The mixed solution was stirred at 0-5 ° C for 2 hours. After addition of benzenesulfonamide (0.39 g, 2.52 mmol) and DBU (0.3 ml), stirring was continued at room temperature for about 6 hours after the completion of the TLC follow-up reaction. The organic phase was washed with NaH2P04 (2 * 5 ml) and saturated brine (2 * 5 ml). The solvent was removed by drying over anhydrous sodium sulfate. The title compound (0.70 g, 80percent yield) was obtained by silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1).
  • 59
  • [ 2922-45-4 ]
  • [ 51146-57-7 ]
  • Pyridine-3-sulfonic acid [(R)-2-(4-isobutyl-phenyl)-propionyl]-amide [ No CAS ]
  • 60
  • [ 98-64-6 ]
  • [ 51146-57-7 ]
  • 4-chloro-<i>N</i>-[2-(4-isobutyl-phenyl)-propionyl]-benzenesulfonamide [ No CAS ]
  • 61
  • [ 81363-76-0 ]
  • [ 51146-57-7 ]
  • Propane-2-sulfonic acid [(R)-2-(4-isobutyl-phenyl)-propionyl]-amide [ No CAS ]
  • 62
  • [ 2508-29-4 ]
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  • <i>N</i>-(5-hydroxy-pentyl)-2-(4-isobutyl-phenyl)-propionamide [ No CAS ]
  • 64
  • [ 1520-70-3 ]
  • [ 51146-57-7 ]
  • Ethanesulfonic acid [(R)-2-(4-isobutyl-phenyl)-propionyl]-amide [ No CAS ]
  • 65
  • [ 2216-51-5 ]
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  • (1R,2S,2''R,5R)-2-(4-isobutylphenyl)propionic acid 2-isopropyl-5-methylcyclohexyl ester [ No CAS ]
  • 66
  • [ 4443-23-6 ]
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  • R(-)-N-[2-(4-Isobutyl-phenyl)-propionyl]-2-phthalimidoethanesulfonamide [ No CAS ]
  • 67
  • [ 5680-80-8 ]
  • [ 51146-57-7 ]
  • methyl 3-hydroxy-2-[(2R)-2-(4-isobutylphenyl)propanoyl]amino}propanoate [ No CAS ]
  • 68
  • [ 51146-57-7 ]
  • [ 5680-79-5 ]
  • [(R)-2-(4-Isobutyl-phenyl)-propionylamino]-acetic acid methyl ester [ No CAS ]
  • 69
  • [ 51146-57-7 ]
  • [ 2491-20-5 ]
  • [ 354899-91-5 ]
  • 70
  • [ 51146-57-7 ]
  • [ 18598-63-5 ]
  • methyl (R)-2-[(2R)-2-(4-isobutylphenyl)propanoyl]amino}-3-mercaptopropanoate [ No CAS ]
  • 71
  • [ 51146-57-7 ]
  • [ 14316-06-4 ]
  • (R)-2-[(R)-2-(4-Isobutyl-phenyl)-propionylamino]-propionic acid methyl ester [ No CAS ]
  • 72
  • [ 51146-57-7 ]
  • [ 114978-05-1 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 4h;Heating / reflux; (R) (-) -ibuprofen (2g, 9.69 mmol) is dissolved in thionyl chloride (4 mL), and the solution obtained is refluxed for 4 hours. After cooling to room temperature, the solvent is evaporated at reduced pressure, and the excess of thionyl chloride is eliminated by dissolving the residue twice with dioxane and evaporating the solvents at a high vacuum. The oily yellow residue (2.34 g; 9.34 mmol) thus obtained, is dissolved in dry dichloromethane (3 mL) and added, by means of slow dripping and in an inert-gas atmosphere, to a solution of 2, 2-dimethyl-1, 3-dioxan-2,5- dione (Meldrum's acid) (1. 35 g ; 9.34 mmol) and pyridine (1. 83 ML ; 22.9 mmol) in dry dichloromethane (7.5 mL) previously cooled to 0-5C with a water/ice bath. Once the additions are completed, the product is left for one hour at this temperature and then for another hour at room temperature. The mixture diluted with dichloromethane is partitioned with a 2N HCI and crushed ice, under vigorous stirring for 30 min. After separation of the phases, the organic phase, washed with 2N HCI (2X10 ML) and with a saturated solution of NACI, is dried on NA2SO4. After evaporation of the solvents at reduced pressure, 2. 69 G OF R (+)-5- [2- (4-ISOBUTYL-PHENYL)-PROPION-1-YL]-2, 2-DIMETHYL-1, 3-dioxan-4,6-dione is obtained as an oil. ( [0. 0] = + 61. 7 ; c = 1% CH2C12) which, without further purifications, is dissolved in dioxane (10 mL). Glacial acetic acid (0.84 mL) and water (0.13 mL) are added, and the resulting solution is heated to the reflux temperature for 3 hours. After cooling and evaporation of the solvents, the residue is purified by means of flash chromatography (eluent : n-hexane/ethyl ether 9: 1) to yield (R) (-)-3- [ (4'- isobutyl) phenyl] butan-2-one as a pale yellow oil (0.97 g; 4.75 mmol). [(X] D =-216 1 (C=1 ; CH3CH20H) ;'H-NMR (CDC13) : 8 6.95 (s, 4H); 3.61 (q, 1H, J=8Hz); 2.3 (d, 3H, J=7Hz); 1.93 (s, 3H); 1.75 (M, 1H) ; 1.26 (d, 2H, J=8Hz); 0.85 (d, 6H, J=7Hz).
With thionyl chloride; In 1,4-dioxane; for 3h;Heating / reflux; (R) (-) -ibuprofen (1. 2 G, 5.8 mmol) is dissolved in dioxane (5 ML) ; thionyl chloride (2.36 mL) is added and the solution obtained is refluxed and left to reflux for 3 hours. After cooling to room temperature, the solvent is evaporated at reduced pressure, and the excess of thionyl chloride is eliminated, dissolving the residue twice with dioxane and evaporating the solvents under high vacuum. An oily yellow residue (1.3 g; 5.79 mmol) is obtained, which is dissolved in dry dichloromethane (2 mL) and added, by means of slow dripping and in an inert atmosphere, to a solution of 2, 2-dimethyl-1, 3-dioxan-2,5-dione (Meldrum's acid) (0. 83 g ; 5.79 mmol) and pyridine (1. 12 ML ; 14 MMOL) in dry dichloromethane (5 mL) previously cooled to T=+5C with a water/ice bath. Once the additions are completed, the mixture is left for one hour at this temperature and then for another hour at room temperature. Themixture, diluted with dichloromethane is repartitioned with a 2N solution of HCL and crushed ice, under vigorous stirring for approximately 30 min. After separation of the phases, the organic phase, washed with 2N HC1 (2xlOmL) and with a saturated solution of NACI, is dried on NA2SO4. fter evaporation of the solvent at reduced pressure, the residue of (R) (+)-5- [2- (4-ISOBUTYL- phenyl)-propion-1-yl]-2, 2-dimethyl-1, 3-dioxan-4, 6-DIONE ( [A] D=+62 ; C=1. 1% CH2CL2) without further purifications, is dissolved in methanol (14 mL); the solution is reheated to reflux for 3 hours. After cooling and evaporation of the solvent, the residue is purified by means of flash chromatography (eluent: n-hexane/ethyl ether 8: 2) to yield pure methyl ester of (R) (-)-4- [ (4'-ISOBUTYL) phenyl] -3-oxopentanoic acid as a colourless oil (0.6 g; 2.28 mmol); [A] D=-192. 5 (C=L ; CH30H) ; TH-NMR (CDCI3) : B 7.1 (s, 4H); 3.88 (q, 1H, J=8Hz); 3.67 (s, 3H); 3.47-3. 28 (q, 2H, J=8Hz); 2.45 (d, 2H, J=8Hz); 1.85 (m, 1H) ; 1.40 (d, 3H, J=8Hz); 0.95 (d, 6H, J=7HZ). To a solution in methanol (2 mL) of 0.15 g (0.57 mmol) of said ester is added a solution of IN NAOH (I mL); and the mixture is stirred at room temperature overnight. The solvents are then evaporated at reduced pressure; the residue is dissolved with water (3 mL), and 2N HC1 is added by dripping up to PH=1 the mixture is then extracted with ethyl ether (3X10 ML) ; the organic phase is then washed with a saturated solution of NACI (10 mL), dried on NA2SO4, and evaporated at reduced pressure to yield 0.12 g (0.48 mmol) of pure (+) 4- [ (4'-isobutyl) phenyl] -3-oxopentanoic acid, as a colourless oil; 'H-NMR (CDC13) : 8 7.1 (m 4H); 3.88 (q, 1H, J=8Hz); 3.45 (m, 2H); 2.48 (d, 2H, J=8Hz); 1. 90 (m, 1H) ; 1.45 (d, 3H, J=8Hz); 0.90 (d, 6H, J=7Hz).
With thionyl chloride; for 3h;Reflux; General procedure: 2-aryl-propionyl chlorides of formula V (general procedure). A solution of 72.8 mmol of a 2-arylpropionic acid of formula V [for example, (R)-2-(4-isobutylphenyl)propionic acid, (R) (-).ibuprofen, 72.8 mmol] in thionyl chloride (37.5 mL) is refluxed for 3 hrs. The mixture is cooled at r. t.; the excess reagent is evaporated to dryness in vacuum; then, twice in succession, small amounts of anhydrous dioxane are added and evaporated to dryness under high vacuum conditions to fully eliminate any residual thionyl chloride. The final oily residue is used in the following reactions. IR (film) cm-1: 1800 (ClC=O)
550 mg With thionyl chloride; In dichloromethane; at 60℃;Cooling with ice; Compound 57-1 (500 mg, 2.427 mmol) was dissolved in 10 mL of dry dichloromethane. After cooling in an ice bath, 5 mL of thionyl chloride was slowly added, and the mixture was stirred at 60 C. overnight. The reaction was monitored by LC-MS until completion. The reaction solution was concentrated to give 550 mg of oily Compound 57-2 which was used directly in the next Step. MS m/z (ESI): N/A.

  • 73
  • [ 51146-57-7 ]
  • [ 62-53-3 ]
  • 2-(4-isobutyl-phenyl)-<i>N</i>-phenyl-propionamide [ No CAS ]
  • 74
  • [ 51146-57-7 ]
  • [ 929-06-6 ]
  • <i>N</i>-[2-(2-hydroxy-ethoxy)-ethyl]-2-(4-isobutyl-phenyl)-propionamide [ No CAS ]
  • 75
  • [ 51146-57-7 ]
  • [ 107-95-9 ]
  • 3-[(R)-2-(4-Isobutyl-phenyl)-propionylamino]-propionic acid [ No CAS ]
  • 76
  • [ 51146-57-7 ]
  • [ 56-12-2 ]
  • 4-[(R)-2-(4-Isobutyl-phenyl)-propionylamino]-butyric acid [ No CAS ]
  • 77
  • [ 6672-69-1 ]
  • [ 51146-57-7 ]
  • 6,7-dihydro-5H-dibenzo[c,e]azepine 2-(4-isonbutylphenyl)-propanoyl amide [ No CAS ]
  • 78
  • [ 71-23-8 ]
  • [ 15687-27-1 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • (R)-ibuprofen 1-propyl ester [ No CAS ]
  • 79
  • [ 771-61-9 ]
  • [ 51146-57-7 ]
  • pentafluorophenyl (R)-2-(4-isobutylphenyl)propionate [ No CAS ]
  • 80
  • [ 51146-57-7 ]
  • [ 2216-51-5 ]
  • ibuprofen (-)-mentyl ester [ No CAS ]
  • 81
  • [ 175591-23-8 ]
  • [ 51146-57-7 ]
  • C27H39NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 48.25h; (R)-2-(4-lsobutylphenyl)propanoic acid (Ibuprofen, 881 mg, 4.275 mmol) was dissolved in dichloromethane (15 mL). 4,4-Dimethylaminopyridine (47.3 mg, 0.387 mmol) and 3-((2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl)phenol (1.0 g, 4.5 mmol) were added. The solution was cooled to 0 0C and dicyclohexylcarbodiimide (1.3 g, 6.3 mmol) in dichloromethane (5 mL) was added. The solution was stirred for 15 min at 0 0C followed by stirring for 48 hours at ambient temperature. The reaction mixture was filtered, the filtrate was washed with 0.5 M aqueous hydrochloric acid and aqueous NaHCO3 (10 percent), dried over sodium sulfate and the solvent was removed in vacuo to obtain a white solid (2.0 g) which was further purified by <n="28"/>conventional chromatographic methods.
  • 82
  • [ 51407-46-6 ]
  • [ 51146-56-6 ]
  • [ 51146-57-7 ]
  • 83
  • [ 51146-57-7 ]
  • (R) (-)-3-[(4'-isobutyl)phenyl]butan-2-one [ No CAS ]
  • 84
  • [ 51146-57-7 ]
  • 2-(4-isobutyl-phenyl)-<i>N</i>,<i>N</i>-dimethyl-propionamide [ No CAS ]
  • 85
  • [ 51146-57-7 ]
  • (R)-N-methyl-2-(4-isobutyl phenyl)-propionamide [ No CAS ]
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