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[ CAS No. 27298-98-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 27298-98-2
Chemical Structure| 27298-98-2
Chemical Structure| 27298-98-2
Structure of 27298-98-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 27298-98-2 ]

CAS No. :27298-98-2 MDL No. :MFCD00145246
Formula : C9H13N Boiling Point : -
Linear Structure Formula :- InChI Key :UZDDXUMOXKDXNE-QMMMGPOBSA-N
M.W : 135.21 Pubchem ID :7015759
Synonyms :

Calculated chemistry of [ 27298-98-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.89
TPSA : 26.02 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) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 1.55
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 2.19
Log Po/w (SILICOS-IT) : 2.07
Consensus Log Po/w : 1.89

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.25 mg/ml ; 0.00927 mol/l
Class : Soluble
Log S (Ali) : -1.71
Solubility : 2.66 mg/ml ; 0.0197 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.83
Solubility : 0.2 mg/ml ; 0.00148 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 27298-98-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P210-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405 UN#:2735
Hazard Statements:H314-H227 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 27298-98-2 ]

* 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 [ 27298-98-2 ]

[ 27298-98-2 ] Synthesis Path-Downstream   1~85

  • 2
  • (1S,2R)-1-Phenyl-2-[1-p-tolyl-eth-(E)-ylideneamino]-propan-1-ol [ No CAS ]
  • [ 27298-98-2 ]
  • [ 586-70-9 ]
  • 3
  • (1R,2S)-1-Phenyl-2-[1-p-tolyl-eth-(E)-ylideneamino]-propan-1-ol [ No CAS ]
  • [ 27298-98-2 ]
  • [ 586-70-9 ]
  • 4
  • [ 27298-98-2 ]
  • [ 533-60-8 ]
  • [ 109-77-3 ]
  • [ 177499-68-2 ]
  • 5
  • [ 27298-98-2 ]
  • C36H45N2O10P [ No CAS ]
  • Phosphoric acid 4-{(S)-2-acetylamino-2-[(S)-3-methyl-1-((S)-1-p-tolyl-ethylcarbamoyl)-butylcarbamoyl]-ethyl}-phenyl ester dibenzyl ester [ No CAS ]
  • 6
  • [ 27298-98-2 ]
  • (+-)-3<i>endo</i>-bromo-2-oxo-bornane-sulfonic acid-(8) [ No CAS ]
  • [ 5344-58-1 ]
  • 7
  • [ 27298-98-2 ]
  • 1-(4-<i>tert</i>-butyl-phenyl)-5-oxo-pyrrolidine-3-carbonyl chloride [ No CAS ]
  • [ 158898-08-9 ]
  • [ 158898-09-0 ]
  • 9
  • [ 27298-98-2 ]
  • [ 53-86-1 ]
  • 2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1<i>H</i>-indol-3-yl]-<i>N</i>-(1-<i>p</i>-tolyl-ethyl)-acetamide [ No CAS ]
  • 10
  • [ 4548-45-2 ]
  • [ 27298-98-2 ]
  • (S)-5-nitro-N-(1-(4'-methylphenyl)ethyl)pyridin-2-amine [ No CAS ]
  • 11
  • [ 22980-09-2 ]
  • [ 27298-98-2 ]
  • 2-(1<i>H</i>-indol-3-yl)-2-oxo-<i>N</i>-(1-<i>p</i>-tolyl-ethyl)-acetamide [ No CAS ]
  • 12
  • [ 54582-23-9 ]
  • [ 27298-98-2 ]
  • [ 586-70-9 ]
  • 13
  • [ 27298-98-2 ]
  • [ 883-55-6 ]
  • 2-(5-chloro-1<i>H</i>-indol-3-yl)-2-oxo-<i>N</i>-(1-<i>p</i>-tolyl-ethyl)-acetamide [ No CAS ]
  • 14
  • [ 27298-98-2 ]
  • [ 6953-35-1 ]
  • 2-(5-nitro-1<i>H</i>-indol-3-yl)-2-oxo-<i>N</i>-(1-<i>p</i>-tolyl-ethyl)-acetamide [ No CAS ]
  • 15
  • [ 5190-68-1 ]
  • [ 27298-98-2 ]
  • quinazolin-4-yl-(1-<i>p</i>-tolyl-ethyl)-amine [ No CAS ]
  • 16
  • [ 27298-98-2 ]
  • [ 108-24-7 ]
  • (S)-N-[1-(4-methylphenyl)ethyl]acetamide [ No CAS ]
  • 18
  • [ 42070-98-4 ]
  • [ 27298-98-2 ]
  • [ 586-70-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; C15H13O4S(1-)*K(1+); C16H15O4S(1-)*K(1+); C16H15O5S(1-)*K(1+); In water; isopropyl alcohol;Resolution of racemate;Product distribution / selectivity; Resolutions Performed with Potassium Chalcon-sulfonates IGeneral Procedure[0061] The sulfonate or mixture of sulfonates (1 mmol) obtained in example 14 was suspended in 1,0 mL 10% HCl. The racemate was added (1 mmol) and 1 mL of iPrOH. The mixture was heated until clear. The salt was removed by filtration under suction and washed with little iPrOH. The salt was analyzed by HPLC to determine the e.e. The results are depicted in the following table. The values in parentheses are after recrystallization. Yields are calculated with respect to the racemate.[0062] Resolution of DL-leucine[0063] with a (1:1:1) mixture of Ia, Ib and Ic; ee=99%; yield=14%.[0064] Resolution of DL-phenylglycine[0065] with a (1:1) mixture of Ia and If; ee=80% (94%); yield 66%[0066] with a (1:1) mixture of Ib and Id; ee=70% (96%); yield (12%)[0067] with a (1:1) mixture of If and Ih; ee=57%[0068] with Ib; ee=24%; yield=46%[0069] Resolution of DL-p-methyl-[alpha]-methylbenzylamine[0070] with a (1:1:1) mixture of Ia, Ib and Ic; ee=60%; yield=30%[0071] with Ib; ee 22%; yield>50%[0072] Resolution of DL-p-hydroxyphenylglycine[0073] with a (1:1) mixture of Ia and If; ee=49%; yield 22%.
With hydrogenchloride; C16H15O5S(1-)*K(1+); In water; isopropyl alcohol;Resolution of racemate;Product distribution / selectivity; Resolutions Performed with Potassium Chalcon-sulfonates IGeneral Procedure[0061] The sulfonate or mixture of sulfonates (1 mmol) obtained in example 14 was suspended in 1,0 mL 10% HCl. The racemate was added (1 mmol) and 1 mL of iPrOH. The mixture was heated until clear. The salt was removed by filtration under suction and washed with little iPrOH. The salt was analyzed by HPLC to determine the e.e. The results are depicted in the following table. The values in parentheses are after recrystallization. Yields are calculated with respect to the racemate.[0062] Resolution of DL-leucine[0063] with a (1:1:1) mixture of Ia, Ib and Ic; ee=99%; yield=14%.[0064] Resolution of DL-phenylglycine[0065] with a (1:1) mixture of Ia and If; ee=80% (94%); yield 66%[0066] with a (1:1) mixture of Ib and Id; ee=70% (96%); yield (12%)[0067] with a (1:1) mixture of If and Ih; ee=57%[0068] with Ib; ee=24%; yield=46%[0069] Resolution of DL-p-methyl-[alpha]-methylbenzylamine[0070] with a (1:1:1) mixture of Ia, Ib and Ic; ee=60%; yield=30%[0071] with Ib; ee 22%; yield>50%[0072] Resolution of DL-p-hydroxyphenylglycine[0073] with a (1:1) mixture of Ia and If; ee=49%; yield 22%.
With chiral stationary phase including isopropyl-functionalized CF6; In methanol; acetic acid; triethylamine; acetonitrile; at 0℃;Purification / work up; In addition to the foregoing, numerous other chromatographic separations using a column bonded with a CSP including a derivatized cyclofructan residue were carried out. Tables 5-9 list some additional examples of chromatographic separations using a column bonded with a CSP of the present invention. AU examples of chromatographic separations using columns bonded with CSPs of the present invention were carried out using the following experimental conditions and procedures.|0132| The high performance liquid chromatography (HPLC) column packing system was composed of an air driven fluid pump (HASKEL, DSTV- 122), an air compressor, a pressure regulator, a low pressure gauge, two high-pressure gauges (10,000 and 6,000 psi), a slurry chamber, check valves, and tubings. The CSPs were slurry packed into a 25 cm x 0.46 cm (inner diameter, I. D.) stainless steel column.|0133| The HPLC system was an Agilent 1 100 system (Agilent Technologies, Palo Alto,CA), which consisted of a diode array detector, an autosampler, a binary pump, a temperature- controlled column chamber, and Chemstation software. All chiral analytes were dissolved in ethanol, methanol, or other appropriate mobile phases, as indicated. For the LC analysis, the injection volume and flow rate were 5 muL and 1 mL/min, respectively. Separations were carried out at room temperature (~20 0C) if not specified otherwise. The wavelengths of UV detection were 195, 200, 210, and 254 nm. The mobile phase was degassed by ultrasonication under vacuum for 5 min. Each sample was analyzed in duplicate. Three operation modes (the normal phase mode, polar organic mode, and reversed phase mode) were tested, unless indicated otherwise. In the normal phase mode, heptane with ethanol or isopropanol was used as the mobile phase. In some cases, trifluoroacetic acid (TFA) was used as an additive, as indicated. The mobile phase of the polar organic mode was composed of acetonitrile/methanol and small amounts of acetic acid and triethylamine. Water/acetonitrile or acetonitrile/acetate buffer (20 mM, pH = 4.1 ) was used as the mobile phase in the reversed-phase mode.|0134| Two different supercritical fluid chromatographic instruments were used. One was a Berger SFC unit with an FCM 1200 flow control module, a TCM 2100 thermal column module, a dual pump control module, and a column selection valve. The flow rate was 4 mL/min. The cosolvent was composed of methanol/ethanol/isopropanol = 1 : 1 : 1 and 0.2% diethylamine (DEA). The gradient mobile phase composition was 5% cosolvent hold during 0- 0.6 min, 5-60% during 0.6-4.3 min, 60% hold during 4.3-6.3 min, 60%-5% during 6.3-6.9 min, and 5% hold during 6.9-8.0 min. The other SFC system was a Jasco (MD, USA) system comprised of an autosampler unit (AS-2059-SF Plus), a dual pump module (PU-2086 Plus), a column thermostat module (CO-2060 Plus), a UV/Vis detector (UV-2075 Plus), and a back pressure regulator module (SCH-Vch-BP). Unless otherwise specified, the mobile phase was composed of CCVmethanol (0.1 % TFA or 0.1% diethylamine). The flow rate was 3 mL/min.|0135| For the calculations of chromatographic data, the "dead time" to was determined by the peak of the refractive index change due to the sample solvent or determined by injecting l ,3,5-tri-/e/-/-butylbenzene in the normal phase mode.
  • 19
  • [ 27298-98-2 ]
  • [ 503071-72-5 ]
  • 2-(4-fluoro-phenyl)-3-[2-(1-<i>p</i>-tolyl-ethylamino)-pyrimidin-4-yl]-6,7-dihydro-5<i>H</i>-pyrazolo[1,2-<i>a</i>]pyrazol-1-one [ No CAS ]
  • 20
  • [ 75-15-0 ]
  • [ 27298-98-2 ]
  • (S,S)-N,N'-bis[1-(4-methylphenylethyl)]thiourea [ No CAS ]
  • 21
  • [ 757195-32-7 ]
  • [ 16355-00-3 ]
  • [ 27298-98-2 ]
  • 22
  • [ 50-00-0 ]
  • [ 27298-98-2 ]
  • [ 120663-39-0 ]
  • C92H116N4O8 [ No CAS ]
  • 23
  • [ 27298-98-2 ]
  • [ 122-00-9 ]
  • (1-<i>p</i>-tolyl-ethyl)-(1-<i>p</i>-tolyl-ethylidene)-amine [ No CAS ]
  • 24
  • [ 937371-81-8 ]
  • [ 27298-98-2 ]
  • 25
  • [ 27298-98-2 ]
  • [ 100-41-4 ]
  • [ 586-70-9 ]
  • 26
  • [ 902131-30-0 ]
  • [ 27298-98-2 ]
  • C19H20N4O3 [ No CAS ]
  • 27
  • [ 27298-98-2 ]
  • [ 78-98-8 ]
  • N-[(S)-1-(4-methylphenyl)ethyl]-2-oxopropan-1-imine [ No CAS ]
  • 28
  • [ 27298-98-2 ]
  • [ 78-98-8 ]
  • N,N-bis[(S)-1-(4-methylphenyl)ethyl]propane-1,2-diimine [ No CAS ]
  • 29
  • [ 54582-23-9 ]
  • [ 27298-98-2 ]
  • 30
  • [ 27298-98-2 ]
  • [ 214195-50-3 ]
  • 31
  • [ 757195-21-4 ]
  • [ 27298-98-2 ]
  • 32
  • [ 104-87-0 ]
  • [ 27298-98-2 ]
  • 33
  • [ 27298-98-2 ]
  • Phosphoric acid mono-(4-{(S)-2-acetylamino-2-[(S)-3-methyl-1-((S)-1-p-tolyl-ethylcarbamoyl)-butylcarbamoyl]-ethyl}-phenyl) ester [ No CAS ]
  • 34
  • [ 27298-98-2 ]
  • 2-Phenyl-9-((S)-1-p-tolyl-ethyl)-9H-pyrimido[4,5-b]indol-4-ylamine [ No CAS ]
  • 35
  • [ 27298-98-2 ]
  • [ 177499-72-8 ]
  • 37
  • [ 2089-33-0 ]
  • [ 27298-98-2 ]
  • 38
  • [ 771544-92-4 ]
  • [ 27298-98-2 ]
  • [ 771544-93-5 ]
YieldReaction ConditionsOperation in experiment
43% Step C: Synthesis of cis-4-[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(1S)-1-(4-methylphenyl)ethyl]cyclohexanecarboxamide hydrochloride. To a suspension of (S)-1-(4-methylphenyl)-ethylamine (12 mg, 1 eq.) and cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino) cyclohexanecarboxylic acid (24 mg, 0.09 mmol) in DCM (2 mL) was added HATU (36 mg, 1.1 eq.). The reaction stirred for 30 seconds at room temperature under argon, and triethylamine (5 drops) was added. The reaction stirred overnight at room temperature. The reaction was diluted with DCM, washed with saturated NaHCO3 (2x) and H2O (1x), and concentrated. Purification by column chromatography (silica gel; DCM:MeOH = 100:0 to 94:6) gave cis-4-(4-Dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexanecarboxylic acid (S)-(1-p-tolyl-ethyl)-amide (15 mg, 43 %). To a solution of the amide in DCM (1 ml_) was added 4M-HCl in dioxane (50 muL,). The reaction was stirred for 30 min at room temperature, and removal of the volatile solvent gave cis-4-[4-(dimethylamino)-5-methylpy-rimidin-2-yl]amino)-N-[(1S-1-(4-methylphenyl)ethyl]cyclohexanecarboxamide hydrochloride as a white powder. ESI MS m/e 396 (M + H)+; 1H NMR (400 MHz, DMSO-d6) 8 11.0 (bs, 1 H), 8.14 (d, 1 H, J = 8.4 Hz), 7.68 (bs, 1 H), 7.54 (s, 1 H), 7.14 (d, 2 H, J = 8.0 Hz), 7.07 (d, 2 H, J = 8.0 Hz), 4.84 (m, 1 H), 4.01 (bs, 1 H), 3.24 (s, 6 H), 2.27 (m, 1 H), 2.25 (s, 3 H), 2.22 (s, 3 H), 1.80-1.54 (m, 8 H), 1.29 (d, 3 H, J = 6.8 Hz).
  • 39
  • [ 32315-10-9 ]
  • [ 27298-98-2 ]
  • N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-[(1S)-1-(4-methylphenyl)ethyl]urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% Example 41: N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-[(1S)-1-(4-methylphenyl)ethyl]urea 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (70 mg) was dissolved in chloroform (1 ml) and triethylamine (0.1 ml) to prepare a solution. A solution of triphosgene (33 mg) in chloroform (0.2 ml) was then added to the solution, and the mixture was stirred at room temperature for 75 min. Next, a solution of (1S)-1-(4-methylphenyl)ethylamine (31 mg) in chloroform (0.2 ml) was added thereto, and the mixture was stirred at room temperature for 10 hr. The stirred mixture was purified by chromatography on silica gel using chloroform/methanol for development to give the title compound (52 mg, yield 48%). 1H-NMR (CDCl3): 1.49 (3H, d, J = 6.83 Hz), 2.33 (3H, s), 4.02 (3H, s), 4.03 (3H, s), 4.53 (1H, m), 5.15 (1H, d, J = 6.83 Hz), 6.41 (1H, d, J = 5.37 Hz), 6.68 (1H, s), 7.07 (2H, d, J = 8.78 Hz), 7.15 (2H, d, J = 7.81 Hz), 7.24 (2H, d, J = 7.81 Hz), 7.35 (2H, d, J = 8.78 Hz), 7.40 (1H, s), 7.54 (1H, s), 8.45 (1H, d, J = 5.37 Hz)
YieldReaction ConditionsOperation in experiment
Examples of suitable chiral auxiliaries include (but are not limited to) the following: ... (R) or (S)-2-phenylglycinol, (R) or (S)-1-(4-bromophenyl)ethylamine, (R) or (S)-alpha-methyl-4-nitrobenzylamine, (R) or (S)-1-phenylpropylamine, (R) or (S)-1-(P-tolyl)ethylamine, (R) or (S)-1-aminoindan, (R) or (S)-1-phenyl-2-(p-tolyl)ethylamine, (R) or (S)-1-aminotetralin, ...
STR18 17.8 g (0.085 mol) of (S)-(-)-N-phenylcarbamate lactic acid and 27.0 g (0.2 mol) of racemic 1-(4-methyl-phenyl)-ethylamine are added to a mixture of 230 g of toluene and 120 g of methanol at 30 C. with stirring. After the mixture has been stirred for a further 1 hour at 30 C., 229.7 g of solvent are distilled off at a maximum sump temperature of 30 C. with gradual reduction of the pressure. The reaction mixture is then cooled to room temperature and filtered with suction. The resulting solid is washed with toluene and dried. This gives, in quantitative yield, based on (S)-(-)-N-phenylcarbamate lactic acid used, the (R)-1-(4-methyl-phenyl)-ethylamine salt of (S)-(-)-N-phenylcarbamate lactic acid which, according to gas-chromatographic analysis, has an optical purity of 100%. The mother liquor produced after the solid has been removed contains the (S)-1-(4-methyl-phenyl)-ethylamine which has not been precipitated as salt, having an S:R isomer ratio of 90.1:9.9.
  • 41
  • [ 317364-83-3 ]
  • [ 27298-98-2 ]
  • [ 317824-15-0 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 52 2-[(S)-1-(4-Methylphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine 2-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine was reacted with <strong>[27298-98-2](S)-1-(4-methylphenyl)ethylamine</strong> according to the procedure described in EXAMPLE 1, Step C to afford the title compound. Mass Spectrum (ESI): m/e 330.3 (M+1). 1H NMR (500 MHz, CDCl3): delta partial 8.53 (s, 1H); 8.39 (d, J=5.3 Hz, 1H), 7.84 (d, J=8.3 Hz, 1H); 6.78 (d, J=5.5 Hz, 1H); 5.75 (br s, 1H); 5.20 (br s, 1H); 2.36 (s, 3H); 1.63 (d, J=6.8 Hz, 3H).
  • 42
  • [ 1120-71-4 ]
  • [ 27298-98-2 ]
  • 3-[(1S)-1-(4-methylphenyl)ethyl]amino}propane-1-sulfonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In 3,3-dimethyl-butan-2-one; toluene; for 4h;Heating / reflux; Preparation of 3-[(1S)-1-(4-methylphenyl)ethyl]amino}propane-1-sulfonic acid (Compound NX); To a solution of (1S)-(-)-1-(4-methylphenyl)ethylamine (5.00 g, 37.0 mmol) in Pinacolone (24 mL) and Toluene (24 mL) was added 1,3-propane sultone (4.30 g, 35.2 mmol). The solution was stirred at reflux for 4 hours. The reaction mixture was cooled to room temperature. The solid was collected by filtration and was washed with acetone (2×25 mL). The solid was suspended in EtOH (60 mL). The suspension was stirred at reflux for 1 hour. The mixture was cooled to room temperature, the solid material was collected by filtration, washed with acetone (2×25 mL) and dried in a vacuum oven at 50 C., affording the title compound, 7.72 g (85%). 1H NMR (D2O, 500 MHz) delta ppm 7.22 (m, 4H), 4.26 (q, 1H, J=6.8 Hz), 2.97 (m, 1H), 2.80 (m, 3H), 2.22 (s, 3H), 1.92 (m, 2H), 1.53 (d, 3H, J=6.8 Hz). 13C (D2O, 125 MHz) delta ppm 140.38, 132.79, 130.09, 127.71, 58.34, 48.06, 44.34, 21.50, 20.41, 18.31. [alpha]D=-26.4 (c=0.0019 in water), ES-MS 256 (M-1).
  • 43
  • [ 393057-88-0 ]
  • [ 27298-98-2 ]
  • (2S)-2-hydroxy-5-(4-methoxyphenyl)pentanoic acid (S)-tolylethylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetone;Heating / reflux; Using (S)-tolylethylamine, (2S)-2-hydroxy-5-(4-methoxyphenyl)pentanoic acid having an optical purity of 97%e.e. was obtained from the compound of Reference Example 3 as starting material by a process similar to the process described in Reference Example 4. The optical purity was determined by the method described in Reference Example 4. 1H-NMR (CDCl3) delta 1.66-1.92(m,4H), 2.61 (m, 1H), 3.78(s,3H), 4.26(m, 1H), 6.80-6.85(m,2H), 7.03-7.12(m,2H).
  • 44
  • [ 915134-70-2 ]
  • [ 27298-98-2 ]
  • D-2-acetylamino-3,3-bis(4-fluorophenyl)propanoic acid (S)-(-)-1-(4-methylphenyl)ethylamine salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20 - 60℃; for 20h; Example 10; Synthesis of D-2-acetylamino-3,3-bis(4-fluorophenyl)propanoic acid?(S)-(-)-1-(4-methylphenyl)ethylamine salt; A solution (10 mL) of 2-acetylamino-3,3-bis(4-fluorophenyl)propanoic acid (4.85 g, 15.3 mmol) in methanol was heated to 60 C., and (S)-(-)-1-(4-methylphenyl)ethylamine (2.19 mL, 15.3 mmol) was added. The mixture was cooled to 20 C. over 4 hours with stirring and stirred for 16 hours. The precipitated crystals were collected by filtration and dried to give the title compound (2.96 g).
  • 45
  • [ 50-00-0 ]
  • [ 27298-98-2 ]
  • [ 69367-61-9 ]
  • 46
  • [ 1067652-68-9 ]
  • [ 27298-98-2 ]
  • [ 1067652-30-5 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0℃; for 4.5h; Example 34 Step a(li?.2i?.4y)-4-(Methanesulfonyl-methyl-aminoV2-((y)-l-p-tolyl-ethylcarbamoylV cyclopentanecarboxylic acid methyl ester (34a); Compound 13f (21 mg, 0.06 mmol) was dissolved in DCM (0.8 mL). Triethylsilane (20 muL, 0.12 mmol) and TFA (0.4 mL) were added and the reaction mixture was stirred for 2.5 h. The solution was concentrated and then dissolved in DMF (1 mL). (5)-(-)-alpha-4-dimethyl benzylamine (11 muL, 0.07 mmol), TEA (26 muL, 0.18 mmol) and HOBt (12 muL, 0.09 mmol) were added and cooled to 0 0C. EDC (16 mg, 0.08 mmol) was added and the reaction mixture was stirred for 4.5 h. The solution was co -evaporate with toluene and then concentrated. The residue was purified using flash column chromatography (toluene/ethyl acetate 1 :2) which gave the title compound (24 mg, 96 %) as an oil. <n="111"/>1H-NMR (300 MHz, CDCl3): delta 1.45 (d, J= 7.2 Hz, 3H), 2.01 -2.19 (m, 4H), 2.33 (s, 3H), 2.78- 2.87 (m, IH), 2.79 (overlap, s, 3H), 2.82 (overlap, s, 3H), 3.13-3.21 (m, IH), 3.72 (s, 3H), 4.83 (m, IH), 5.04 (app. quintet, J= 7.2 Hz, IH), 6.17 (d, J= 7.5 Hz, IH), 7.13-7.20 (m, 4H); 13C- NMR (75.5 MHz, CDCl3): 521.2, 22.0, 28.5, 31.0, 32.4, 37.6, 45.3, 46.4, 49.0, 52.5, 56.3, 126.1, 129.5, 137.3, 140.2, 171.7, 174.9.
  • 47
  • [ 17640-21-0 ]
  • [ 42070-98-4 ]
  • [ 296236-17-4 ]
  • [ 27298-98-2 ]
YieldReaction ConditionsOperation in experiment
45%; 45% With Novozym 435; at 23℃; for 3h;Molecular sieve; Enzymatic reaction; General procedure: One of the amines rac-1a-i (2 mmol) and isopropyl methoxyacetate (2 mmol) were added into a reaction vessel containing Novozym 435 (25 mg) and molecular sieves (4 A, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 C) if not otherwise stated. The reaction was stopped by filtering off the enzyme at (50 +/- 0.5)% conversion. Isolation of the products was performed by silica gel chromatography using a mixture of hexane and ethylacetate and/or mixture of dichloromethane and methanol as eluent.
  • 48
  • [ 3938-96-3 ]
  • [ 42070-98-4 ]
  • [ 296236-17-4 ]
  • (S)-N-[1-(p-tolyl)ethyl]-2-methoxyacetamide [ No CAS ]
  • [ 27298-98-2 ]
  • 49
  • [ 27298-98-2 ]
  • [ 42070-98-4 ]
  • [ 52726-41-7 ]
  • 50
  • [ 4282-34-2 ]
  • [ 27298-98-2 ]
  • [ 709613-20-7 ]
YieldReaction ConditionsOperation in experiment
71% a) Synthesis of (S)-5-(1-p-Tolyl-ethylcarbamoyl)-thiophene-2-carboxylic Acid Methyl Ester A solution of 1.4 g (7.5 mmol) of methyl thiophen-2,5-dicarboxylate in CH2Cl2 (5 ml) is treated with 1.5 ml (18 mmol) thionylchloride and one drop of DMF and subsequently heated at 80 C. for 1 hour.The solvent and excess of thionylchloride are evaporated under reduced pressure, and the residue is dissolved in CH2Cl2 (10 ml) and treated slowly with (S)-1-(p-tolyl)ethylamine (1.0 g, 7.4 mmol) in CH2Cl2 (10 ml) and triethylamin (2 ml, 14.2 mmol).Stirring at rt is continued for 1 additional hour.The product is isolated after acidic work-up and recrystallisation as yellow solid (mp=165 C.) in 71% yield (1.6 g).
  • 52
  • [ 27298-98-2 ]
  • [ 431-03-8 ]
  • [ 1229648-64-9 ]
  • 53
  • [ 27298-98-2 ]
  • [ 3282-30-2 ]
  • [ 444169-18-0 ]
  • 54
  • [ 1257422-02-8 ]
  • [ 27298-98-2 ]
  • [ 1257422-13-1 ]
  • [ 1257422-12-0 ]
YieldReaction ConditionsOperation in experiment
In methanol; di-isopropyl ether;Reflux; Resolution of racemate; Example 2b Resolution using the enantiomers of MePEA The racemic phthalic acid monoester (+/-)-3 (30.0 g, 87.63 mmol) and (S)-(-)-MePEA (11.85 g, 87.6 mmol) were added to a diisopropyl ether/methanol mixture (9:1 v/v; 330 ml) and the mixture heated to reflux. The suspension thus obtained was cooled to room temperature and maintained under stirring for 8-10 hours. The solid thus formed was filtered off and dried at 25 C under reduced pressure to obtain 23.50 g of a white solid (PP1). The mother liquors were evaporated under reduced pressure (40 ºC/15 mbar) to give 17.61 g of an oil (ML). After the usual displacement of the base, HPLC analyses of ML and PP1 displayed the following composition: ML (S)-3/(R)-3 =89.5 : 10.5; PP1 (S)-3/(R)-3 =22 : 78. The PP1 solid was suspended in diisopropyl ether/methanol (9:1 v/v; 190 ml) and heated to reflux for ten minutes then left to cool to room temperature and maintained under stirring for 4-8 hours. The solid was filtered off and dried under reduced pressure to obtain 19.45 g of a salt (PP2). Evaporation under reduced pressure (40 ºC/15 mbar) of the precipitation solvent gave 3.98 g of a residue (WL1). HPLC analyses of the PP2 and WL1 samples after the usual displacement of the base displayed, respectively, the following composition (S)-3/(R)-3 = 11 : 89 and (S)-3/(R)-3 = 76.5 : 23.5. Washing PP2 under hot conditions with a diisopropyl ether/methanol mixture (9:1 v/v; 190 ml) gave, after cooling and filtering, 18.14 g of a salt, PP3, whose composition after displacement was (S)-3/(R)-3 = 8.3 : 91.7. Evaporation of the filtrate gave 1.30 g of a residue (WL2) whose composition, after displacement of the base, was (S)-3/(R)-3 = 54 : 46.
  • 55
  • [ 27298-98-2 ]
  • [ 29949-69-7 ]
  • ((BH3)(tert-butyl)(phenyl)phosphine)(1-(p-tolyl)ethyl)amine [ No CAS ]
  • ((BH3)(tert-butyl)(phenyl)phosphine)(1-(p-tolyl)ethyl)amine [ No CAS ]
  • 56
  • [ 13292-87-0 ]
  • [ 27298-98-2 ]
  • [ 29949-69-7 ]
  • ((BH3)(tert-butyl)(phenyl)phosphine)(1-(p-tolyl)ethyl)amine [ No CAS ]
  • ((BH3)(tert-butyl)(phenyl)phosphine)(1-(p-tolyl)ethyl)amine [ No CAS ]
  • 57
  • [ 1312949-25-9 ]
  • [ 27298-98-2 ]
  • [ 1312949-26-0 ]
YieldReaction ConditionsOperation in experiment
50% To a solution of 2-((3-chloro-1 ,4-dimethyl-1 H-pyrazolo[3,4-b]pyridin-6-yl)oxy)acetic acid in DMF (5 ml) was added HATU (1.03 g, 2.72 mmol) and DIPEA (1.2 ml, 6.81 mmol). After 20 min at rt, (S)-1-(p-tolylethan)amine (0.43 ml, 2.95 mmol) was added to the miyture. After 16 h, water was added and the mixture extracted with CH2CI2. The organic phases were dried over Na2S04 and the solvent removed under reduced pressure. Purification by column chromatography (eluent 60% hexane in EtOAc) yielded 420 mg (50%) of the title compound.[1H-NMR (DMSO-de, 600 MHz) delta 8.51 (d, 1 H), 7.16 (d, 2H), 7.05 (d, 2H), 6.63 (s, 1H), 4.93 (t, 1 H), 4.83 (d, 1 H), 4.79 (d, 1 H), 3.77 (s, 3H), 2.60 (s, 3H), 2.25 (s, 3H), 1.35 (d, 3H); UPLC- MS Rtj = 1.15 min; [M+H]+ = 373.1 , 375.1]
  • 58
  • [ 27298-98-2 ]
  • [ 78-98-8 ]
  • (1S,2S)-(-)-N1,N2-bis[1-(4-methylphenyl)ethyl]-1,2-propanediimine [ No CAS ]
  • 59
  • [ 1379536-97-6 ]
  • [ 27298-98-2 ]
  • [ 1379537-03-7 ]
  • 60
  • 3-(4-methylpentyloxy)-4-methoxy-phenyl isocyanate [ No CAS ]
  • [ 27298-98-2 ]
  • [ 1362627-56-2 ]
  • 61
  • [ 27298-98-2 ]
  • [ 94-36-0 ]
  • [ 1374682-84-4 ]
  • 62
  • [ 1401298-94-9 ]
  • [ 27298-98-2 ]
  • [ 1401299-02-2 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; General procedure: To the solution of keto-acid 8 (100 mg, 0.36 mmol) in diethyl ether (5 mL) was added an equivalent of optically pure amine. Upon the addition, the precipitate formed immediately. The resulted suspension was filtered by suction to give the salt, which was then recrystallized from methanol. 3.2.3 (S)-(-)-1-p-Tolylethylamine salt of keto-acid 8 Mp 162-164 C (Methanol). 1H NMR (400 MHz, CD3OD): delta 7.89 (d, J=8.5 Hz, 2H), 7.83 (d, J=8.5 Hz, 2H), 7.19 (d, J=8.0 Hz, 2H), 7.10 (d, J=8.0 Hz, 2H), 4.26 (q, J=6.9 Hz, 1H), 3.56 (m, 1H), 2.20 (s, 3H), 1.51 (m, 2H), 1.47 (d, J=6.9 Hz, 3H), 1.41 (m, 2H), 1.18 (m, 2H), 0.76 (d, J=6.5 Hz, 6H), 0.75 (d, J=6.5 Hz, 6H). 13C NMR (100 MHz, CD3OD): delta 206.7 (+), 174.0 (+), 143.5 (+), 140.1 (+), 139.9 (+), 136.9 (+), 130.8 (-), 130.5 (-), 128.8 (-), 127.6 (-), 52.0 (-), 43.5 (-), 43.3 (+), 27.4 (-), 23.3 (-), 23.1 (-), 21.2 (-), 20.8 (-). IR (KBr) numax: 2957, 2869, 2546, 2187, 1674, 1648, 1581, 1392, 1245, 816, 792, 727 cm-1. LRMS (ESI): 412 [M++1], 349, 312, 271, 136, 119. Anal. calcd for C26H37NO3: C, 75.87; H, 9.06; N, 3.40. Found: C, 76.00; H, 9.20; N, 3.46.
  • 63
  • [ 27298-98-2 ]
  • [ 2004-06-0 ]
  • N6-[(S)-1-(4-methylphenyl)ethyl]adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In propan-1-ol; at 80℃; for 7h; A mixture of (S)-1-(4-methylphenyl)-ethylamine (568 mg) and 6-chloropurine riboside (300 mg) in PrOH (50 ml) was heated to 80C for 7 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over Sephadex LH-20 gel and eluted with ethanol to yield N6-[(S)-1-(4-methylphenyl)-ethyl]-adenosine(320 mg) as a white solid: positive ESIMS mlz 386 [M + H]+ and 408 [M + Na]+; negative ESIMS mlz 384 [M - H]-; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.36 (1H, s, H-2), 8.26 (1H, brs, -NH), 8.14 (1H, s, H-8), 5.86 (1H, d, J= 6.0 Hz, H-1'), 5.42 (1H, d, J= 6.3 Hz, -OH), 5.36 (1H, m, -OH), 5.17 (1H, d, J = 4.8 Hz, -OH), 4.57 (1H, m, H-2'), 4.12 (1H, m, H-3'), 3.94 (1H, m, H-4'), 3.64 (1H, m, H-5'a), 3.54 (1H, m, H-5'b); the (S)-1-(4-methylphenyl)-ethyl moiety delta 7.30 (2H, s, H-2', H-6'), 7.07 (2H, s, H-3', H-5'), 5.48 (1H, m, H-7'), 2.22 (3H, s, -CH3), 1.50 (3H, s, H-8'); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety delta 153.9 (s, C-6), 152.3 (d, C-2), 148.6 (s, C-4), 139.8 (d, C-8), 119.7 (s, C-5), 87.9 (d, C-1'), 85.9 (d, C-4'), 73.6 (d, C-2'), 70.7 (d, C-3'), 61.7 (t, C-5'); part for (S)-1-(4-methylphenyl)-ethyl moiety delta 142.2 (s, C-1'), 135.6 (s, C-4'), 128.7 (d, C-2', C-6'), 126.1(d, C-3', C-5'), 48.6 (d, C-7' ), 22.5 (q, C-8'), 20.7 (q, -CH3).
320 mg In propan-1-ol; at 80℃; for 7h; A mixture of (S)-1-(4-methylphenyl)-ethylamine (568 mg) and 6-chloropurine riboside (300 mg) in PrOH (50 ml) was heated to 80 C. for 7 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over Sephadex LH-20 gel and eluted with ethanol to yield N6-[(S)-1-(4-methylphenyl)-ethyl]adenosine (320 mg) as a white solid: positive ESIMS m/z 386 [M+H]+ and 408 [M+Na]+; negative ESIMS m/z 384 [M-H]-; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.36 (1H, s, H-2), 8.26 (1H, brs, -NH), 8.14 (1H, s, H-8), 5.86 (1H, d, J=6.0 Hz, H-1'), 5.42 (1H, d, J=6.3 Hz, -OH), 5.36 (1H, m, -OH), 5.17 (1H, d, J=4.8 Hz, -OH), 4.57 (1H, m, H-2'), 4.12 (1H, m, H-3'), 3.94 (1H, m, H-4'), 3.64 (1H, m, H-5'a), 3.54 (1H, m, H-5'b); the (S)-1-(4-methylphenyl)-ethyl moiety delta 7.30 (2H, s, H-2", H-6"), 7.07 (2H, s, H-3", H-5"), 5.48 (1H, m, H-7"), 2.22 (3H, s, -CH3), 1.50 (3H, s, H-8"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety delta 153.9 (s, C-6), 152.3 (d, C-2), 148.6 (s, C-4), 139.8 (d, C-8), 119.7 (s, C-5), 87.9 (d, C-1'), 85.9 (d, C-4'), 73.6 (d, C-2'), 70.7 (d, C-3'), 61.7 (t, C-5'); part for (S)-1-(4-methylphenyl)-ethyl moiety delta 142.2 (s, C-1"), 135.6 (s, C-4"), 128.7 (d, C-2", C-6"), 126.1 (d, C-3", C-5"), 48.6 (d, C-7"), 22.5 (q, C-8"), 20.7 (q, -CH3).
320 mg In propan-1-ol; at 80℃; for 7h; (S)-1-(4-methylphenyl) -ethylamine (568 mg) was dissolved in normal propyl alcohol (50 mL), 6-chloropurine nucleoside (300 mg) Heat up to 80 C and react for 7 h. The solvent was recovered in the reaction solution, chromatographed through a gel column and eluted with ethanol to obtain white solid N6-[(S)-1-(4-methylphenyl)-ethyl]-adenosine (320 mg) It was
  • 64
  • [ 33458-88-7 ]
  • [ 27298-98-2 ]
  • [ 1262893-98-0 ]
YieldReaction ConditionsOperation in experiment
97% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; at 20℃; for 0.5h; General procedure: The 6-methoxy-9-oxo-9H-xanthene-2-carboxylic acid (1) (100 mg, 0.37 mmol) was dissolved in dry tetrahydrofuran (20 mL) and triethylamine (103 muL, 0.74 mmol) was added. Following, TBTU (120 mg, 0.37 mmol) and an appropriate chiral reagent (0.37 mmol) were added. The mixture was stirred at room temperature for 30 min (4) or 2 h (2-3). After completion of the reaction, the solvent was evaporated under reduced pressure and the crude product was dissolved in dichloromethane (50 mL). This solution was washed with 1M HCl solution (2 × 25 mL), saturated solution of NaHCO3 (2 × 30 mL) and water (3 × 50 mL). The organic layer was dried with anhydrous sodium sulphate, filtered and the solvent was evaporated under reduced pressure. The product was recrystallized from ethanol (2) or ethyl acetate/n-hexane (3-4), to afford the chiral xanthone derivative.
97% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; at 20℃; for 0.5h; General procedure: 6-Methoxy-9-oxo-9H-xanthene-2-carboxylic acid (1) or 2-((9-oxo-9H-xanthen-3-yl)oxy)acetic acid (2) (100 mg, 0.37 mmol) was dissolved in anhydrous THF (20 mL) and TEA (103 muL, 0.74 mmol) was added. Following, TBTU (120 mg, 0.37 mmol) and an appropriate chiral reagent (0.37 mmol) were added. The mixture was stirred at room temperature for 0.5 to 5 h. After completion of the reaction, the solvent was evaporated under reduced pressure and the crude product was dissolved in 50 mL of dichloromethane (3-10, 13-14, 17-30), ethyl acetate (11-12) or chloroform (15-16, 31-32). This solution was washed with 1M HCl solution (2×25 mL), saturated solution of NaHCO3 (2×30 mL), and water (3×50 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The product was recrystallized from ethyl acetate/n-hexane (3-4, 7-14, 19-20, 23-30), EtOH (5-6, 21-22), chloroform/n-hexane (15-16, 31-32), or MeOH/water (17-18) to afford the chiral derivative of xanthone. Compounds 3-32 were identified by their spectroscopic and analytical data.
  • 65
  • [ 70249-37-5 ]
  • [ 122-00-9 ]
  • [ 3886-69-9 ]
  • [ 27298-98-2 ]
  • [ 99-06-9 ]
  • 66
  • [ 27298-98-2 ]
  • C36H28BNO3 [ No CAS ]
  • 67
  • [ 27298-98-2 ]
  • C36H28BNO3 [ No CAS ]
  • 68
  • [ 27298-98-2 ]
  • [ 1422527-15-8 ]
  • 69
  • [ 27298-98-2 ]
  • C36H28BNO3 [ No CAS ]
  • 70
  • [ 27298-98-2 ]
  • [ 123-11-5 ]
  • [ 1422527-24-9 ]
  • 71
  • [ 27298-98-2 ]
  • [ 123-11-5 ]
  • C17H19NO [ No CAS ]
  • 73
  • [ 943779-00-8 ]
  • [ 27298-98-2 ]
  • [ 943779-11-1 ]
  • 74
  • [ 27298-98-2 ]
  • [ 13750-81-7 ]
  • (S)-[(1-methyl-1H-imidazol-2-ylmethylene)-(1-(4-methylphenyl)-ethanamine)] [ No CAS ]
  • 75
  • [ 23020-15-7 ]
  • [ 27298-98-2 ]
  • [ 1531592-27-4 ]
  • 76
  • [ 25363-95-5 ]
  • [ 27298-98-2 ]
  • [ 1542743-76-9 ]
YieldReaction ConditionsOperation in experiment
96% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; at 20℃; for 0.5h; General procedure: 6-Methoxy-9-oxo-9H-xanthene-2-carboxylic acid (1) or 2-((9-oxo-9H-xanthen-3-yl)oxy)acetic acid (2) (100 mg, 0.37 mmol) was dissolved in anhydrous THF (20 mL) and TEA (103 muL, 0.74 mmol) was added. Following, TBTU (120 mg, 0.37 mmol) and an appropriate chiral reagent (0.37 mmol) were added. The mixture was stirred at room temperature for 0.5 to 5 h. After completion of the reaction, the solvent was evaporated under reduced pressure and the crude product was dissolved in 50 mL of dichloromethane (3-10, 13-14, 17-30), ethyl acetate (11-12) or chloroform (15-16, 31-32). This solution was washed with 1M HCl solution (2×25 mL), saturated solution of NaHCO3 (2×30 mL), and water (3×50 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The product was recrystallized from ethyl acetate/n-hexane (3-4, 7-14, 19-20, 23-30), EtOH (5-6, 21-22), chloroform/n-hexane (15-16, 31-32), or MeOH/water (17-18) to afford the chiral derivative of xanthone. Compounds 3-32 were identified by their spectroscopic and analytical data.
  • 77
  • [ 27298-98-2 ]
  • [ 1559065-82-5 ]
  • 78
  • [ 27298-98-2 ]
  • [ 604-60-4 ]
  • [ 557-20-0 ]
  • C76H76N4O4Zn2 [ No CAS ]
  • 79
  • [ 27298-98-2 ]
  • [ 1542703-67-2 ]
  • 80
  • [ 27298-98-2 ]
  • [ 1542703-76-3 ]
  • 81
  • [ 27298-98-2 ]
  • [ 1542703-81-0 ]
  • 82
  • [ 27298-98-2 ]
  • [ 583-53-9 ]
  • [ 1336235-55-2 ]
  • 83
  • [ 27298-98-2 ]
  • [ 6633-28-9 ]
  • (S)-4-methyl-3,5-dinitro-N-(1-(p-tolyl)ethyl)benzamide [ No CAS ]
  • 84
  • [ 27298-98-2 ]
  • [ 99-33-2 ]
  • [ 186345-18-6 ]
  • 85
  • [ 27298-98-2 ]
  • 4-[(9R)-4-chloro-9-hydroxy-9-(trifluoromethyl)-9H-fluoren-2-yloxy]butyric acid [ No CAS ]
  • (1S)-1-(4-methylphenyl)ethylamine salt of 4-[(9R)-4-chloro-9-hydroxy-9-(trifluoromethyl)-9H-fluoren-2-yloxy]butyric acid [ No CAS ]
  • 4-[(9S)-4-chloro-9-hydroxy-9-(trifluoromethyl)-9H-fluoren-2-yloxy]butyric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.6 g In ethyl acetate; at 20 - 60℃;Inert atmosphere; Step 8 (1S)-1-(4-Methylphenyl)ethylamine salt of 4-[(9R)-4-chloro-9-hydroxy-9-(trifluoromethyl)-9H-fluoren-2-yloxy]butyric acid [0140] (1S)-1-(4-methylphenyl)ethylamine (19.5 g) was dissolved in ethyl acetate (720 ml), and 4-[(9R)-4-chloro-9-hydroxy-9-(trifluoromethyl)-9H-fluoren-2-yloxy]butyric acid (72.5 g) was added. The reaction mixture was stirred at 60 C. for 2 hr, and at room temperature overnight. The precipitated solid was collected by filtration, and washed with ethyl acetate (100 ml). The obtained solid was dried under reduced pressure at 60 C. for 5 hr to give the title compound (68.6 g). In addition, 4-[(9S)-4-chloro-9-hydroxy-9-(trifluoromethyl)-9H-fluoren-2-yloxy]butyric acid could be obtained from the filtrate. (Optical Purity) [0142] The optical purity of 4-[(9R)-4-chloro-9-hydroxy-9-(trifluoromethyl)-9H-fluoren-2-yloxy]butyric acid was determined under the HPLC analysis condition 1 (optical purity 90.2% e.e.). Retention time of (R) form 12.9 min, retention time of (S) form 10.4 min. [0143] 1H-NMR (400 MHz, DMSO-D6) delta: 8.14 (1H, d, J=7.7 Hz), 7.66 (1H, d, J=7.7 Hz), 7.53 (1H, td, J=7.6, 1.1 Hz), 7.40 (1H, td, J=7.6, 1.0 Hz), 7.26 (2H, d, J=7.9 Hz), 7.16-7.10 (4H, m), 4.08 (2H, t, J=6.5 Hz), 4.01 (1H, q, J=6.7 Hz), 2.32 (2H, t, J=7.3 Hz), 2.26 (3H, s), 1.98-1.91 (2H, m), 1.26 (3H, d, J=6.7 Hz).
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