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CAS No.: | 1012341-50-2 |
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Name: | (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid |
Article Data: | 25 |
Molecular Structure: | |
Formula: | C23H29NO4 |
Molecular Weight: | 383.488 |
Synonyms: | (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid;LCZ696 inter.;(2R,4S)-5-(Biphenyl-4-yl)-4-[(tert-butoxycarbonyl)aMino]-2-Methylpentanoic acid;(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic;(2R,4S)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(4-phenylphenyl)pentanoic acid;LCA696 inter;[1,1'-Biphenyl]-4-pentanoic acid, γ-[[(1,1-dimethylethoxy)carbonyl]amino]-α-methyl-, (αR,γS) |
EINECS: | -0 |
Density: | 1.115±0.06 g/cm3(Predicted) |
Boiling Point: | 582.6±50.0 °C(Predicted) |
PSA: | 75.63000 |
LogP: | 5.29110 |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
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Stage #1: C33H38N2O5 With dihydrogen peroxide In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With lithium hydroxide at 25 - 30℃; for 3h; | 95% |
(2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
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With ammonium formate; nickel(II) acetate tetrahydrate; (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine In ethanol at 55℃; for 8h; Temperature; | 91.9% |
With hydrogen under 15001.5 - 18751.9 Torr; | 90% |
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)-α-(dimethylamino)benzyl]ferrocene In ethanol at 40℃; under 15001.5 Torr; for 6h; Product distribution / selectivity; | 86.9% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
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Stage #1: C33H38N2O5 With dihydrogen peroxide In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With lithium hydroxide In tetrahydrofuran; water at 20 - 25℃; for 3h; | 90% |
(3R,5S)-5-biphenyl-4-ylmethyl-3-methyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
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With sodium hydroxide at 60℃; Reagent/catalyst; | 86% |
Stage #1: (3R,5S)-5-biphenyl-4-ylmethyl-3-methyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester With lithium hydroxide In tetrahydrofuran; water at 20℃; for 1h; Stage #2: With phosphoric acid In tetrahydrofuran; water Product distribution / selectivity; |
di-tert-butyl dicarbonate
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
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Stage #1: (R)-2-methyl-4-hydroxyimino-5-(4-biphenyl)pentanoic acid With ((+)-(1R)-[1,1'-binaphthalene]-2,2'-diylbis[diphenylphosphine-κP])chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+) chloride; hydrogen In methanol at 40℃; under 30003 Torr; Autoclave; Stage #2: di-tert-butyl dicarbonate With lithium hydroxide Reflux; diastereoselective reaction; | 80% |
(R)-5-(biphenyl-4-yl)-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid
cyclohexylamine
A
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
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Stage #1: (R)-5-(biphenyl-4-yl)-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid With palladium 10% on activated carbon; hydrogen In ethanol; water at 40℃; under 3750.38 Torr; for 3h; Stage #2: cyclohexylamine In Isopropyl acetate at 70℃; | A 58% B 10% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
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With (S)-1-(1-Naphthyl)ethylamine In methanol at 60℃; for 1h; Temperature; | 37% |
With (S)-1-phenyl-ethylamine In ethanol at 20℃; for 2h; |
(2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid
B
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
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With diiodo(p-cymene)ruthenium(II) dimer; (SP,S′P)-1,1′-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2′-bis[(R)-α-(dimethylamino)benzyl]ferrocene; hydrogen In ethanol at 75℃; under 22502.3 Torr; | A 5.3% B 93.66 %Chromat. |
With diiodo(p-cymene)ruthenium(II) dimer; (SP,S′P)-1,1′-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2′-bis[(R)-α-(dimethylamino)benzyl]ferrocene; hydrogen In dichloromethane; water at 60℃; under 45004.5 Torr; for 16h; Autoclave; Ionic liquid; Inert atmosphere; | A n/a B n/a |
(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid hydrochloride
di-tert-butyl dicarbonate
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
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Stage #1: (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid hydrochloride; di-tert-butyl dicarbonate With potassium carbonate In water; isopropyl alcohol at 20℃; for 1h; Stage #2: With phosphoric acid In water; isopropyl alcohol Product distribution / selectivity; |
(3R,5S)-5-biphenyl-4-ylmethyl-3-methyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
B
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: sodium hydride; potassium hexamethylsilazane / toluene / 1 h / -15 °C 1.2: 0.5 h / -15 °C 1.3: 1 h / 20 °C 2.1: water; lithium hydroxide / tetrahydrofuran / 20 h / 20 °C 3.1: triethylamine; hydrogen / 5% rhodium-on-charcoal / Isopropyl acetate / 20 °C / 760.05 Torr View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride; potassium hexamethylsilazane / toluene; mineral oil / 1 h / -15 °C 1.2: 0.5 h / -15 °C 1.3: 1 h / 20 °C 2.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C 3.1: hydrogen; triethylamine; 10% Pt/activated carbon / Isopropyl acetate / 20 °C / 760.05 Torr View Scheme |