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CAS No. : | 1012341-50-2 | MDL No. : | MFCD27955981 |
Formula : | C23H29NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YNELJETWNMPEEH-UZLBHIALSA-N |
M.W : | 383.48 | Pubchem ID : | 46193546 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
90% | With hydrogen; under 15001.5 - 18751.9 Torr; | 7) To 61.4g (R, E) -5-([1,1'-biphenyl] -4-yl) -4-((tert-butoxycarbonyl) amino) -2-methyl-2-pentene acidHydrogen is introduced (hydrogen partial pressure is 2-2.5 MPa), and hydrogenation catalyzes to obtain 55.2g (2R, 4S) -5- (biphenyl-4-yl) -4-[(Tert-butoxycarbonyl) amino] -2-methylpentanoic acid;(90% yield); |
86.9% | With hydrogen;diiodo(p-cymene)ruthenium(II) dimer; (SP,S?P)-1,1?-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2?-bis[(R)-alpha-(dimethylamino)benzyl]ferrocene; In ethanol; at 40.0℃; under 15001.5 Torr; for 6.0h;Product distribution / selectivity; | Example 2: (2R,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid in crystalline form; [Show Image] To a suspension of <strong>[1012341-48-8](E)-(R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid</strong> (200 g, 524.3 mmol) in degassed ethanol (900 ml) at 40 C a solution of diiodo(p-cymene)ruthenium(II) dimer (0.052 g, 0.0524 mmol) and (alphaR,alphaR)-2,2'-bis(alpha-N,N-dimethylaminophenylmethyl)-(S,S)-1,1'-bis[di(3,5-dimethyl-4-methoxyphenyl)phosphine]ferrocene (= Mandyphos SL-M004-1) (0.116 g, 0.110 mmol) was added in degassed ethanol (100 ml). The solution was degassed using vacuum and a pressure of 20 bar hydrogen applied. The mixture was stirred at 40 C for 6 h. Vessel was then purged with nitrogen. Ethanol (700 ml) was removed by distillation. Isopropyl acetate (600 ml) was added. Solvent (600 ml) was removed by distillation. Isopropyl acetate (600 ml) was added. Solvent (600 ml) was removed by distillation. Isopropyl acetate (300 ml) was added and the solution heated to reflux. Heptane fraction (1200 ml) was added and the mixture cooled to room temperature. The solid was collected by filtration and washed with heptane fraction-isopropyl acetate 2 : 1 mixture (360 ml). The solid was dried overnight at 50 C under 1-50 mbar vacuum to afford (2R,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid (174.7 g, 86.9 %) as a white/off-white solid. Mpt 146-147 C; deltaH (500 MHz; DMSO) 1.07 (3H, d, J 7.0, 1-CH3), 1.34 (9H, s, (CH3)3), 1.38 (1H, m, 3-HA), 1.77 (1H, m, 3-HB), 2.43 (1H, m, 2-H), 2.70 (2H, d, J 7.0, 5-H), 3.69 (1H, m, 4-H), 6.74 (1H, d, J 9.0, NH), 7.27 (2H, d, J 8.0, Ar-ortho-H(Ph)), 7.36 (1H, t, J 7.0, Ar-(Ph)-para-H), 7.46 (2H, t, J 7.5, Ar-(Ph)-meta-H), 7.57 (2H, d, J 8.0, Ar-meta-H(Ph), 7.64 (2H, d, J 7.5, Ar-(Ph)-ortho-H), 12.01 (1H, s, CO2H); deltac (500 MHz, DMSO) 18.1 (1-CH3), 28.3 [(CH3)3], 35.9 (2-C), 37.9 (3-C), 40.7 (5-C), 50.0 (4-C), 77.4 [(C(CH3)3], 126.3, 126.5, 127.2, 128.9, 129.8 (Ar-CH), 137.7 (Ar-ipso-C(Ph)), 138.3 (Ar-para-C(Ph)), 140.1 (Ar-(Ph)-ipso-C), 155.2 (NCO), 177.2 (CO2H); mlz (+ESI) 406 ([MNa]+, 6%), 384 ([MH]+, 31), 328 (100), 284 (19); Found: [MH]+, 384.21691. C23H30NO4 requires MH 384.21693. Figure 1 shows the structure of crystalline (2R,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid measured by x-ray diffraction. The crystals comprise the following unit cell dimensions, measured by 100 K: |
73.8% | With palladium 10% on activated carbon; hydrogen; In ethanol; at 25.0℃; under 7500.75 Torr; for 20.0h; | (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methyl-pentane was added to the hydrogenation vessel with stirring. 2-enoic acid (Compound III) (75 g, 0.20 mol), 10% palladium on carbon (Pd/C) (3.0 g) and 750 ml of ethanol,Hydrogen was introduced and allowed to react (1.0 MPa, 25 C) for 20 hours. Filter and concentrate to dryness,It was recrystallized by adding an appropriate ratio of isopropyl acetate/petroleum ether, and dried to give a white solid (Compound II). |
With diiodo(p-cymene)ruthenium(II) dimer; (SP,S?P)-1,1?-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2?-bis[(R)-alpha-(dimethylamino)benzyl]ferrocene; hydrogen; sodium hydroxide; In dichloromethane; water; at 60.0℃; under 30003 Torr; for 16.0h;Autoclave; Ionic liquid; Inert atmosphere; | General procedure: [Ru(p-cimene)I2]2 (4.85 mg; 4.96 mumol) and (SP,S?P)-1,1?-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2?-bis[(R)-alpha-(dimethylamino)benzyl]ferrocene (Mandyphos, SL-M004-1) (12.0mg; 11.4 mumol) were weighted in two Schlenk tubes inside a glovebox. The Ru precursor was dissolved in CH2Cl2 (5 mL) and the resulting solution was transferred into the Schlenk tube containing the ligand and stirred at r.t. for 1 h. The ionic liquid 1-ethyl-3-methylimidazoliumbis(trifluoromethylsulfonyl)imide [EMIM][NTf2] (5 mL) was added and the CH2Cl2 was slowly evaporated under vacuum. An aliquot of this solution (0.2 mL) was diluted with additional [EMIM][NTf2] (1.8 mL) and the solution was transferred into a 13 mL window autoclave. (R)-1-CO2H (100 mg; 262 mumol) was dissolved in a basic aqueous solution (4 mL, pH 13) (see table 2 for detail) and transferred into the autoclave. The autoclave was heated to reaction temperature and pressurized with H2 (40 bar). The reaction was started by magnetic agitation. After 16 h, the autoclave was cooled to r.t. and gently vented. The upper water phase was removed with a needle and neutralized with an HCl solution (1 M), the white solid precipitated was collected by filtration and analyzed by HPLC. | |
With diiodo(p-cymene)ruthenium(II) dimer; hydrogen; In ethanol; under 22502.3 Torr; for 20.0h; | Step 3 0.07853 mol of compound II was added to 130 g of absolute ethanol and 0.030 g of [RuI2] 2 and 0 ? 120 g Mandyphos chiral ligands were added. The hydrogen pressure was 3·0 MPa, and the pressure was stirred for 20 hours. Rate of 95.05%. | |
340 g | With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; N,N?-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; hydrogen; In ethanol; at 40.0℃; under 11251.1 Torr;Autoclave; | To the autoclave is sequentially added in the Embodiment 3: (R, E) -5 - ([1, 1' - biphenyl] -4 - yl) -4 - ((tert-butoxy carbonyl) amino) -2 - methyl -2 - pentenoic acid 381g, ethanol 3.5 kg, double-(dicyclopentadiene) tetra fluoborate rhodium 99 mg and phosphine CK - 04 279 mg, replacing hydrogen, pressure 15 kg, temperature 40 C, stirring to LC in the control reaction is complete, filtering, crude job the filtrate turns on lathe, chiral analysis of II:III=90 the two isomers: 10. The crude product of ethyl acetate and petroleum ether beating, then using ethanol recrystallization, the crude product of ethyl acetate and petroleum ether beating, to obtain the product (2R, 4S) -5 - ([1, 1' - biphenyl] -4 - yl) -4 - ((tert-butoxy carbonyl) amino) -2 - methyl valeric acid 340g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diiodo(p-cymene)ruthenium(II) dimer; (SP,S?P)-1,1?-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2?-bis[(R)-alpha-(dimethylamino)benzyl]ferrocene; hydrogen; In dichloromethane; water; at 60.0℃; under 45004.5 Torr; for 16.0h;Autoclave; Ionic liquid; Inert atmosphere; | General procedure: [Ru(p-cimene)I2]2 (4.85 mg; 4.96 mumol) and (SP,S?P)-1,1?-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2?-bis[(R)-alpha-(dimethylamino)benzyl]ferrocene (Mandyphos, SL-M004-1) (12.0mg; 11.4 mumol) were weighted in two Schlenk tubes inside a glovebox. The Ru precursor was dissolved in CH2Cl2 (5 mL) and the resulting solution was transferred into the Schlenk tube containing the ligand and stirred at r.t. for 1 h. The ionic liquid 1-ethyl-3-methylimidazoliumbis(trifluoromethylsulfonyl)imide [EMIM][NTf2] (5 mL) was added and the CH2Cl2 was slowly evaporated under vacuum. An aliquot of this solution (0.2 mL) was diluted with additional [EMIM][NTf2] (1.8 mL) and the solution was transferred into a 13 mL window autoclave. (R)-1-CO2H (100 mg; 262 mumol) was dissolved in a basic aqueous solution (4 mL, pH 13) (see table 2 for detail) and transferred into the autoclave. The autoclave was heated to reaction temperature and pressurized with H2 (40 bar). The reaction was started by magnetic agitation. After 16 h, the autoclave was cooled to r.t. and gently vented. The upper water phase was removed with a needle and neutralized with an HCl solution (1 M), the white solid precipitated was collected by filtration and analyzed by HPLC. |