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CAS No. :1012341-48-8 MDL No. :MFCD28386950
Formula : C23H27NO4 Boiling Point : No data available
Linear Structure Formula :- InChI Key :JXTNUXJSXXIIFE-VISDOYDDSA-N
M.W : 381.47 Pubchem ID :56846981
Synonyms :

Safety of [ 1012341-48-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
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Application In Synthesis of [ 1012341-48-8 ]

* 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 [ 1012341-48-8 ]

[ 1012341-48-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 149709-59-1 ]
  • [ 1012341-48-8 ]
YieldReaction ConditionsOperation in experiment
70% With ethanol; lithium hydroxide; at 35.0℃; for 1.0h; 6) To 94.6g (4R) -5- [1,1'-biphenyl] -4-yl-4-[[tert-butoxycarbonyl] amino] -2-methyl-2-pentenoic acid ethyl esterAdd 473mL ethanolAnd 13.7g of lithium hydroxide, stirred at 35 for 1h,After the reaction, the crystals were concentrated to obtain 61.4g(R, E) -5-([1,1'-biphenyl] -4-yl) -4-((tert-butoxycarbonyl) amino) -2-methyl-2-pentenoic acid;(70% yield);
With lithium hydroxide; ethanol; Example 1: (E)-(R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid; [Show Image] (E)-(R)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid ethyl ester (CASNo. 149709-59-1) is hydrolysed using lithium hydroxide in ethanol to yield (E)-(R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid. White solid. deltaH (400 MHz; DMSO) 1.31 (9H, s, (CH3)3), 1.59 (3H, s, 1-CH3), 2.68 (1H, dd, J 6.8, 13.2, 5-HA), 2.86 (1H, m, 5-HB), 4.44 (1H, m, 4-H), 6.51 (1H, d, J 9.2, 3-H), 7.16 (1H, d, J 8.0, NH), 7.26 (2H, d, J 8.0, Ar-ortho-H(Ph)), 7.31 (1H, t, J 7.6, Ar-(Ph)-para-H), 7.40 (2H, t, J 8.0, Ar-(Ph)-meta-H), 7.54 (2H, d, J 8.0, Ar-meta-H(Ph), 7.60 (2H, d, J 7.6, Ar-(Ph)-ortho-H), 12.26 (1H, s, CO2H); m/z (+ESI) 404 ([MNa]+, 17%), 382 ([MH]+, 2), 326 (10), 264 (100), 167 (13).
With lithium hydroxide; at 80.0℃; for 1.0h; 0.1833 mol of compound I,1 L of isopropyl acetate,1.00 mol of NaBr,Was added to a 2 L flask,Stirring at 20 C for 30 min,Then the temperature is controlled to 20 C,Add TEMPO;Step 2 Preparation of NaClO-NaHCO3 aqueous solution:1.25 mol of NaHCO3 was dissolved in 360 ml of water,An aqueous NaCl solution containing 0.220 mol of available chlorine was added dropwise to the solution at a temperature of 10-15 C;Step 3 An aqueous solution of NaClO-NaHCO3 prepared in Step 2 was added dropwise to the isopropyl acetate solution of Compound I-NaBr,10-15 temperature drop in 80min,And then adding sodium thiosulfate solution to terminate the reaction,Layered organic phase,Washed with aqueous NaCl solution,To obtain the isopropyl acetate solution of compound II;Step 4 To a solution of compound II in isopropyl acetate,Add phosphorusYe Lide,30 reaction 1h,Add a water to the lemonAcid terminates the reaction,And insulation 0.5h.Dispensing,Washed with organic phase,The compound III was distilled under reduced pressure;Step 5 To the resulting compound III was added 1.3 mol of lithium hydroxide,80 insulation reflux 1h,Cooling crystallization,Filter,Dried to obtain 56.1 g of compound IV dry product,The molar yield was 80.25%Purity 99.30%.TEMPOtempDefinitions of temponounthe speed at which a passage of music is or should be played.Listening to music with a slow tempo helps calm the mind.synonyms: speed, cadence, rhythm, beat, time, pulse, measure, meterthe rate or speed of motion or activity; pace.the tempo of life dictated by a heavy workloadsynonyms: pace, rate, speed, velocityTranslations of temponounspeed, rate, velocity, pace, tempo, quicknessbeat, tempo, time, racket, racquet, tempitempi, tempotempoGoogle Translate for Business:Translator ToolkitWebsite TranslatorGlobal Market Finder
55.4 g With lithium hydroxide; In ethanol; water; at 80.0℃; for 1.0h; Step 1 to 800g95% ethanol and 400g of pure water, the compound I, 1.3mol lithium hydroxide 0.1833mol, 80C insulation reflux 1H, cooled to active carbon is added 9% by weight of Compound I 42 C , heated to reflux for 80 deg.] C incubation 2h. Step 2 was filtered hot, aqueous citric acid was added to the filtrate, the reaction was terminated, 80 deg.] C to reflux IH heat, cooling crystallization, filtration and drying to obtain 55.4 g of dried compound II, molar yield of 79.05%, 99.20% purity.
23.3 g (3) (R,E)-5-((1,1'-biphenyl)-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoic acid ethyl ester Was added 83 g of ethanol, 150 g of water and 4.57 g of lithium hydroxide and heated to reflux, TLC monitoring of raw materials, (R,E)-5-((1,1'-biphenyl)-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoic acid ethyl ester disappear after concentration to dry concentrate; (4) 200 g of water and 25 g of activated clay were added to the concentrate obtained in step (3) and stirred at room temperature for 1 hour, Then filtered, and 250 g of ethanol was added to the filtrate, 11.46 g of acetic acid was added dropwise and heated to reflux for 15 minutes and then cooled to 5 to 10 C Stir, the precipitation of solid is the final product of sand library (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methyl-2-pentenoic acid, 23.3 g, molar yield 79.9%, purity 98.8%, triphenylphosphine oxide content 0.008%.

  • 2
  • [ 1012341-48-8 ]
  • [ 1012341-50-2 ]
YieldReaction ConditionsOperation 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

  • 3
  • [ 1012341-48-8 ]
  • (2S,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% 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 60.0℃; under 4125.41 Torr; for 240.0h;Product distribution / selectivity; Example 3; (2S,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid; [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> (10 g, 26.1 mmol) in degassed ethanol (90 ml) was added a solution of diiodo(p-cymene)ruthenium(II) dimer (0.156 g, 0.16 mmol) and (alphaS,alphaS)-2,2'-bis(alpha-N,N-dimethylaminophenylmethyl)-(R,R)-1,1'-bis[di(3,5-dimethyl-4-methoxyphenyl)phosphine]ferrocene (= Mandyphos SL-M004-2) (0.348 g, 0.33 mmol) in degassed ethanol (30 ml) portion wise over the entire reaction time of 5 days. The solution was degassed using vacuum and a pressure of 5.5 bar hydrogen was applied. The mixture was heated to 60 C and stirred at this temperature for 5 days. Vessel was then purged with nitrogen. Solvent was removed in vacuo. Solid was dissolved in isopropyl acetate (34 ml) and heated to reflux. Heptane fraction (68 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 (20 ml). The solid was dried overnight at 50 C under 1-50 mbar vacuum to afford (2S,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid (4.22 g, 42 %) as a grey solid. deltaH (500 MHz; DMSO) 1.06 (3H, d, J 7.0, 1-CH3), 1.32 (9H, s, (CH3)3), 1.42 (1H, m, 3-HA), 1.78 (1H, m, 3-HB), 2.39 (1H, m, 2-H), 2.73 (2H, d, J 7.0, 5-H), 3.73 (1H, m, 4-H), 6.75 (1H, d, J 9.5, NH), 7.29 (2H, d, J 8.0, Ar-ortho-H(Ph)), 7.35 (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) 16.2 (1-CH3), 28.2 [(CH3)3], 35.7 (2-C), 37.9 (3-C), 40.7 (5-C), 49.2 (4-C), 77.4 [(C(CH3)3], 126.3, 126.5, 127.2, 128.9, 129.7 (Ar-CH), 137.8 (Ar-ipso-C(Ph)), 138.4 (Ar-para-C(Ph)), 140.1 (Ar-(Ph)-ipso-C), 155.3 (NCO), 177.6 (CO2H); m/z (+ESI) 406 ([MNa]+, 4%), 384 ([MH]+, 44), 328 (100), 284 (22); Found: [MH]+, 384.21696. C23H30NO4 requires MH 384.21693.
  • 4
  • [ 1174130-80-3 ]
  • [ 1012341-48-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; triphenylphosphine;tetrakis(triphenylphosphine) palladium(0); In xylene;Reflux; A mixture of (R)-5-Biphenyl-4-yl-4-tert-butoxycarbonyIamino-2-methylenepentanoic acid (0.38 g, 1 mmol, Example 32 in WO 2009/090251), Pd(PPh3)4 (70 mg, 0.06 mmol), PPh3 (31.5 mg, 0.12 mmol) and sodium bicarbonate (0.27 g, 3.2 mmol) in 10 mL xylene is heated to reflux, and stirred overnight to afford (R)-5-Biphenyl-4-yl-4-tert- butoxycarbonylamino-2-methyl-pent-(E)-2-enoic acid as determined by HPLC analysis. Spectroscopic data as reported in Example 1 in WO 2008/031567.HPLC methodColumn: Eclipse XDB-C 8; 150x4.6mm; 5 muiotaeta. Mobile Phase A (0.1 % H3P04) in water; Mobile Phase B (Acetonitrile). Gradient: 0 min (30 % B); 8 min (95 % B); 15 min (95 % B). Flow rate: 1.00 ml min-1 . Wavelength: 210 nm. Temperature: 30 C.Retention time: 8.2 min
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; triphenylphosphine; In 5,5-dimethyl-1,3-cyclohexadiene;Reflux; A mixture of (R)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylenepentanoic acid (0.38 g, 1 mmol, Example 32 in WO 2009/090251), Pd(PPh3)4 (70 mg, 0.06 mmol), PPh3 (31.5 mg, 0.12 mmol) and sodium bicarbonate (0.27 g, 3.2 mmol) in 10 mL xylene is heated to reflux, and stirred overnight to afford (R)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methyl-pent-(E)-2-enoic acid as determined by HPLC analysis. Spectroscopic data as reported in Example 1 in WO 2008/031567.
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