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CAS No. : | 25611-78-3 | MDL No. : | MFCD00008063 |
Formula : | C14H15N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 197.28 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
55% | With sodium hydroxide In dichloromethane Ambient temperature; phase-transfer conditions; Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With ammonia; hydrogen In water at 130℃; for 24h; Autoclave; | |
69% | With ammonium formate; C25H29ClIrN2O3P at 50℃; for 18h; Sealed tube; | |
With formic acid; ammonium carbonate |
Stage #1: phenyl benzyl ketone With ammonium formate at 160℃; Stage #2: With hydrogenchloride In methanol | ||
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / 6 h / 60 °C 2: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In diethyl ether; ethyl acetate | 144 L-Proline, 1-[2-(3,4,5-Trimethoxyphenyl)-2-Oxoethyl] 1,2-Diphenylethylamide Hydrochloride EXAMPLE 144 L-Proline, 1-[2-(3,4,5-Trimethoxyphenyl)-2-Oxoethyl] 1,2-Diphenylethylamide Hydrochloride Following the procedure described in Example 120, the coupling of N-[2-(3,4,5-trimethoxyphenyl)-2-oxoethyl]-L-proline hydrochloride (250 mg, 0.69 mmol) and 1,2-diphenylethylamine (0.40 mL, 2.1 mmol) provided, after treatment with HCl in Et2 O, 95 mg of the hydrochloride salt of L-proline, 1-[2-(3,4,5-trimethoxyphenyl)-2-oxoethyl] 1,2-diphenylethylamide as a powder. Rf=0.56 (free base in EtOAc) LSIMS [M-HCl]=503 (mass calculated for C30 H34 N2 O5 +HCl=539.07). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Nakazaki et al, supra The salt (806.6 mg) was dissolved in 50 mL of IN NaOH and 25 mL of CH2 Cl2. The layers were separated and the aqueous portion was extracted with 2*25 mL of CH2 Cl2. The combined organic layers were washed with 15 ml of 1N NaOH, dried (K2 CO3), and the solvent removed at reduced pressure to give 449.1 mg of (-)-1(R),2-diphenylethylamine as a colorless liquid; [α]D19 =-50.1, C=3.7, EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chiral stationary phase including (R)-naphthylethyl-carbamate-functionalized CF6; In methanol; acetic acid; triethylamine; acetonitrile; at 20℃;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 μL 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Candida antarctica Lipase A; In acetonitrile; at 20℃; for 24.0h;Enzymatic reaction; | The acylation of 5 with CALA was performed with a solution containing 5 (0.2 mmol), CALA on celite (8 mg), and TFEB (3 equiv) in acetonitrile (2 mL) at room temperature for 24 h. (R)-5: [α]25D [α]D25 -5.32 (c 2.0, CHCl3, 57% ee) (lit. [α]D [α]D -10.1 (c 1.96, CHCl3, 91% ee; Eddine, J. J.; Cherqaoui, M. Tetrahedron: Asymmetry 1995, 6, 1225-1228). (S)-6: [α]25D [α]D25 -25.4 (c 2.0, CHCl3, 85% ee). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Pseudomonas stutzeri lipase; In toluene; at 20℃; for 24.0h;Enzymatic reaction; | The acylation of 5 with PSL was performed with a solution containing 5 (0.2 mmol), PSL (40 mg), and EMA (2 equiv) in toluene (2 mL) at room temperature for 24 h. (S)-5: [α]25D [α]D25 +6.55 (c 2.0, CHCl3, 70% ee) (lit. [α]20D [α]D20 +10.7 (c 1.05, CHCl3, >99% ee; Berger, M. L.; Schweifer, A.; Rebernik, P.; Hammerschmidt, F. Bioorg. Med. Chem. 2009, 17, 3456-3462). (R)-6: [α]25D [α]D25 +21.7 (c 1.4, CHCl3, >99% ee). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium carbonate In acetonitrile at 70℃; | 17.1 Step 1:5 - bromo - N - (1, 2 - diphenyl-ethyl) -2 - nitroaniline The 4 - bromo -2 - fluoro -1 - nitrobenzene (500 mg, 2 . 27 mmol), 1, 2 - diphenyl serotonin reuptake (450 mg, 2 . 27 mmol) and potassium carbonate (630 mg, 4 . 54 mmol) dissolved in acetonitrile (10 ml), and heated to 70 °C stirring overnight. Adding water to the reaction solution and in the ethyl acetate extract. Separating the organic layer, salt water for washing, drying with anhydrous sodium sulfate, filtered and concentrated. The residue fast chromatography for separation and purification (petroleum ether/ethyl acetate=8/1), the title compound as a yellow solid from (900 mg, 99%). |