((1-(4-fluorophenyl)vinyl)oxy)trimethylsilane
(4S)-3-(1-oxo-2-propen-1-yl)-4-phenyl-1,3-oxazolidin-2-one
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
With iodine In toluene at 40℃; | 94% |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane at 40℃; for 2h; | 91% |
(S)-4-phenyl-2-oxazolidinone
5-(4-fluorophenyl)-5-oxopentanoic acid
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane | 86% |
Stage #1: 5-(4-fluorophenyl)-5-oxopentanoic acid With dmap; pivaloyl chloride In N,N-dimethyl-formamide at 2 - 20℃; for 1.5h; Stage #2: (S)-4-phenyl-2-oxazolidinone In N,N-dimethyl-formamide at 30 - 35℃; for 2h; | 85.7% |
Stage #1: 5-(4-fluorophenyl)-5-oxopentanoic acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -10℃; for 4h; Evans Aldol Reaction; Inert atmosphere; Stage #2: (S)-4-phenyl-2-oxazolidinone With lithium chloride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 85% |
pivaloyl chloride
5-(4-fluorophenyl)-5-oxopentanoic acid
(S)-5-phenyl-1,3-oxazolidine-2-one
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Stage #1: pivaloyl chloride; 5-(4-fluorophenyl)-5-oxopentanoic acid With dmap In N,N-dimethyl-formamide at 2 - 20℃; for 1.5h; Stage #2: (S)-5-phenyl-1,3-oxazolidine-2-one With dmap In N,N-dimethyl-formamide at 30 - 35℃; for 2h; | 85.7% |
C16H19FO4
(S)-4-phenyl-2-oxazolidinone
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Stage #1: C16H19FO4; (S)-4-phenyl-2-oxazolidinone With dmap In N,N-dimethyl-formamide for 7h; Heating / reflux; Stage #2: With sulfuric acid In water; N,N-dimethyl-formamide for 0.5h; Stage #3: With sodium hydrogencarbonate In water; N,N-dimethyl-formamide | |
With dmap In DMF (N,N-dimethyl-formamide) for 7h; Heating / reflux; |
(S)-4-phenyl-2-oxazolidinone
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: chloro-trimethyl-silane / dichloromethane / 0.5 h / 0 - 10 °C 1.2: 2 h / 0 - 10 °C 1.3: 2 h / 0 - 20 °C 2.1: iodine / toluene / 40 °C View Scheme |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction 3: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C View Scheme | |
Multi-step reaction with 3 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction 3: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C View Scheme |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction 3: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C View Scheme | |
Multi-step reaction with 3 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction 3: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C View Scheme |
(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction 2: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine; dmap / dichloromethane / 4 h / 0 °C 2: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 3: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction 4: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine; dmap / dichloromethane / 4 h / 0 °C 2: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 3: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction 4: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine; dmap / dichloromethane / 4 h / 0 °C 2: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 3: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction 4: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine; dmap / dichloromethane / 4 h / 0 °C 2: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 3: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction 4: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C View Scheme |
1-(4-fluorophenyl)ethanone
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 10 h / 100 °C / Inert atmosphere 2: iodine / toluene / 40 °C View Scheme |
fluorobenzene
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / 5 h / 15 - 30 °C 1.2: 0 - 20 °C 2.1: triethylamine; pivaloyl chloride / dichloromethane 2.2: 13 h / Reflux View Scheme |
glutaric anhydride,
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / 5 h / 15 - 30 °C 1.2: 0 - 20 °C 2.1: triethylamine; pivaloyl chloride / dichloromethane 2.2: 13 h / Reflux View Scheme |
trimethylsilyl cyanide
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
2-(4-fluorophenyl)-6-oxo-6-(2-oxo-4(S)-phenyloxazolidin-3-yl)-2-trimethylsilyloxyhexanenitrile
Conditions | Yield |
---|---|
With iodine In dichloromethane at 0℃; for 2.33333h; | 100% |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
trimethyl orthoformate
(S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one
Conditions | Yield |
---|---|
toluene-4-sulfonic acid In methanol Reflux; | 99.02% |
With sulfuric acid In methanol for 1.5h; Reflux; | 80% |
toluene-4-sulfonic acid In methanol at 20℃; Reflux; | |
With toluene-4-sulfonic acid at 20℃; for 23h; Reflux; |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
Conditions | Yield |
---|---|
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With TarB-N02 In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With lithium borohydride In tetrahydrofuran for 0.666667h; Reagent/catalyst; enantioselective reaction; | 96% |
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at -5 - 0℃; for 4 - 6h; Stage #2: With sulfuric acid; dihydrogen peroxide In methanol; dichloromethane; water; toluene for 0.25h; | 95% |
Stage #1: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at -5 - 0℃; for 0.25h; Stage #2: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione In dichloromethane; toluene at -5 - 0℃; for 4 - 6h; | 95% |
ethylene glycol
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
(S)-3-{4-[2-(4-fluorophenyl)dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one
Conditions | Yield |
---|---|
Stage #1: ethylene glycol; (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione; chloro-trimethyl-silane at 20 - 25℃; for 20h; Stage #2: With water; sodium hydrogencarbonate In toluene at 50℃; for 0.5h; Product distribution / selectivity; | 95% |
With N-Bromosuccinimide; trimethyl orthoformate at 70℃; for 8h; Inert atmosphere; | 95% |
Stage #1: ethylene glycol; (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With toluene-4-sulfonic acid In toluene for 20 - 24h; Heating / reflux; Stage #2: With water; sodium carbonate In toluene at 50℃; Product distribution / selectivity; | 94.9% |
methanol
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
(S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one
Conditions | Yield |
---|---|
With N-Bromosuccinimide; trimethyl orthoformate at 50℃; for 9h; Inert atmosphere; | 91% |
2,2-Dimethyl-1,3-propanediol
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
3-{4-[2-(4-fluorophenyl)-5,5-dimethyl-[1,3]dioxin-2-yl]butyryl}(4S)-phenyl-1,3-oxazolidin-2-one
Conditions | Yield |
---|---|
With phosphorus pentoxide; sulfuric acid In dichloromethane for 5h; Reflux; | 89% |
With Pyridine hydrobromide In toluene at 20 - 115℃; for 5h; Product distribution / selectivity; | |
With chloro-trimethyl-silane In dichloromethane at 20 - 115℃; for 5h; Product distribution / selectivity; |
2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
(S)-3-{4-[2-(4-fluorophenyl)dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one
Conditions | Yield |
---|---|
Stage #1: 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane; (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With trimethylsilyl trifluoromethanesulfonate In toluene at 20 - 50℃; for 3 - 4h; Stage #2: With water; sodium hydrogencarbonate In toluene Product distribution / selectivity; | 89% |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
trimethyleneglycol
(S)-3-[4-[2-(4-fluorophenyl)-[1,3]dioxan-2-yl]-1-oxobutyl]-4-phenyloxazolidin-2-one
Conditions | Yield |
---|---|
With N-Bromosuccinimide; trimethyl orthoformate at 100℃; for 12h; Inert atmosphere; | 86.8% |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one
Conditions | Yield |
---|---|
With borane-THF In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere; | 70% |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
A
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
Conditions | Yield |
---|---|
With borane-THF; boron trifluoride diethyl etherate; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 25℃; Product distribution; Further Variations:; Catalysts; Temperatures; acid additives, water content; | |
With BH3-DEA; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 40℃; |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
A
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate; dimethyl sulfate; N,N-diethylaniline; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 20℃; Product distribution; Further Variations:; Reagents; Temperatures; | A 13 g B n/a |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: (R)-(CH2)3CHCPh2O(B-Me)N; BH3*SMe2 / CH2Cl2 / 2 h / 0 °C 2.1: TiCl4 / CH2Cl2 / 3 h / -35 - -30 °C 3.1: 995 mg / CH2Cl2 / 0.5 h / Heating 4.1: BSA / CH2Cl2 / 0.25 h / 20 °C 4.2: TBAF*3H2O / CH2Cl2 / 90 h / 0 °C 4.3: 90 percent / aq. H2SO4 / propan-2-ol / 1 h View Scheme |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (R)-(CH2)3CHCPh2O(B-Me)N; BH3*SMe2 / CH2Cl2 / 2 h / 0 °C 2: TiCl4 / CH2Cl2 / 3 h / -35 - -30 °C View Scheme |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
C33(13)C6H46F2N2O5Si2
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: (R)-(CH2)3CHCPh2O(B-Me)N; BH3*SMe2 / CH2Cl2 / 2 h / 0 °C 2: TiCl4 / CH2Cl2 / 3 h / -35 - -30 °C 3: 995 mg / CH2Cl2 / 0.5 h / Heating View Scheme |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
A
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
Conditions | Yield |
---|---|
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 18 - 20℃; for 1h; Stage #2: With water; potassium carbonate In tetrahydrofuran; toluene at 20 - 30℃; for 0.5h; | |
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With sodium tetrahydroborate; chloro-trimethyl-silane; (R)-α,α-diphenylprolinol In tetrahydrofuran at 24℃; for 3h; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 4℃; for 0.5h; Product distribution / selectivity; | A n/a B n/a |
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With sodium tetrahydroborate; chloro-trimethyl-silane; (R)-2-[bis(4-trifluorophenyl)hydroxymethyl]pyrrolidine In tetrahydrofuran at 24℃; for 3h; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 4℃; for 0.5h; Product distribution / selectivity; | A n/a B n/a |
With chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II); formic acid/triethylamine complex 5:2 In tert-butyl methyl ether at 42℃; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; stereoselective reaction; | A n/a B n/a |
isopropyl alcohol
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
Conditions | Yield |
---|---|
With magnesium sulfate In triethanolamine(chloride) |
hydroxylamine hydrochloride
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
With potassium carbonate In isopropyl alcohol for 2 - 4h; Reflux; |
N-methoxylamine hydrochloride
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
C21H21FN2O4
Conditions | Yield |
---|---|
With triethylamine In ethanol at 80 - 85℃; for 10h; |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
C41H34F2N2O7
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / 23 h / 20 °C / Reflux 2.1: dichloromethane; toluene / 0.83 h / -33 - -30 °C 2.2: 3.5 h / -33 °C 3.1: acetic acid; sodium dihydrogencitrate / dichloromethane; toluene / 0.58 h / -33 °C View Scheme |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
C41H36F2N2O7
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / 23 h / 20 °C / Reflux 2.1: dichloromethane; toluene / 0.83 h / -33 - -30 °C 2.2: 3.5 h / -33 °C 3.1: acetic acid; sodium dihydrogencitrate / dichloromethane; toluene / 0.58 h / -33 °C 4.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 4.2: 1.67 h / Inert atmosphere 4.3: 0.17 h View Scheme |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / 23 h / 20 °C / Reflux 2.1: dichloromethane; toluene / 0.83 h / -33 - -30 °C 2.2: 3.5 h / -33 °C View Scheme |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydroxylamine hydrochloride / pyridine / 0 - 20 °C 2.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 0 °C 2.2: -15 °C 3.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 60 °C 3.2: 8 h / 60 °C 3.3: 20 h / 20 °C 4.1: hydrogenchloride; formaldehyd / water; tetrahydrofuran / 6 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: hydroxylamine hydrochloride / pyridine / 0 - 20 °C 2.1: dmap; 1H-imidazole / dichloromethane / 0.17 h / 20 °C 2.2: 5 h 3.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 0 °C 3.2: 3 h / -15 °C 4.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 60 °C 4.2: 8 h / 60 °C 5.1: hydrogenchloride; formaldehyd / water; tetrahydrofuran / 4 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: phosphorus pentoxide; sulfuric acid / dichloromethane / 5 h / Reflux 2: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -5 °C 3: N,O-Bis(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / toluene / 48 h / Reflux 4: formic acid / dichloromethane / 12 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / hexane / 6 h / 25 °C 2: N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride / toluene / 60 °C View Scheme |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With hydroxylamine hydrochloride In pyridine at 0 - 20℃; Stage #2: With hydrogenchloride In water; ethyl acetate Product distribution / selectivity; |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride / pyridine / 0 - 20 °C 2.1: dmap; 1H-imidazole / dichloromethane / 0.17 h / 20 °C 2.2: 5 h 3.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 0 °C 3.2: 3 h / -15 °C View Scheme |
Molecular Structure of (4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone (CAS NO.189028-93-1):
Molecular formula: C20H18FNO4
Molecular Weight: 355.36
H bond acceptors: 5
H bond donors: 0
Freely Rotating Bonds: 6
Polar Surface Area: 63.68Å2
Index of Refraction: 1.578
Molar Refractivity: 91.64 cm3
Molar Volume: 275.8 cm3
Surface Tension: 50.6 dyne/cm
Density: 1.288 g/cm3
Flash Point: 297.6 °C
Enthalpy of Vaporization: 85.3 kJ/mol
Boiling Point: 568.4 °C at 760 mmHg
Vapour Pressure: 6.19E-13 mmHg at 25°C
Product Categories: Intermediate of ezetimibe
SMILES: Fc1ccc(cc1)C(=O)CCCC(=O)N3C(=O)OC[C@@H]3c2ccccc2
InChI: InChI=1/C20H18FNO4/c21-16-11-9-15(10-12-16)18(23)7-4-8-19(24)22-17(13-26-20(22)25)14-5-2-1-3-6-14/h1-3,5-6,9-12,17H,4,7-8,13H2/t17-/m1/s1
(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone , with CAS number of 189028-93-1, can be called 2-Oxazolidinone,3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-, (4S)- (9CI) ; 2-Oxazolidinone,3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-, (S)- ; (4S)-4-Phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one ; (S)-3-[4-(4-Fluorobenzoyl)-1-oxobutyl]-4-phenyloxazolidin-2-one ; (S)-3-[5-(4-Fluorophenyl)-1,5-dioxopentyl]-4-phenyloxazolidin-2-one .
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