C14H18N4O4
atazanavir
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate In water at 5 - 40℃; | 100% |
{(S)-1-[N'-((2S,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
atazanavir
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane | 95% |
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate In water at 5 - 40℃; for 1.5 - 2h; | 95% |
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
atazanavir
Conditions | Yield |
---|---|
With pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 35℃; for 1.5h; Temperature; Concentration; | 91.6% |
(S)-{2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester
methyl [(2S)-3,3-dimethyl-1-({(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate
atazanavir
Conditions | Yield |
---|---|
In dichloromethane for 64h; Silica gel; | 87% |
silica gel In dichloromethane for 64h; | 87% |
In isopropyl alcohol at 90℃; for 12h; |
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
atazanavir
Conditions | Yield |
---|---|
With 4-methyl-morpholine; diisopropyl-carbodiimide In dichloromethane; isopropyl alcohol at -10 - 20℃; Product distribution / selectivity; Inert atmosphere; | 84% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 22 - 25℃; Reagent/catalyst; Large scale; | 82.1% |
With O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight; Yield given. Multistep reaction; |
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane
atazanavir
Conditions | Yield |
---|---|
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With thionyl chloride; triethylamine In dichloromethane at 42℃; for 3h; Stage #2: 1-[4-(pyridine-2-yl)phenyl]-(5S)-2,5-diamino-(4S)-hydroxy-6-phenyl-2-azahexane In dichloromethane at 20℃; Solvent; Temperature; Concentration; | 74.2% |
atazanavir
Conditions | Yield |
---|---|
With sodium tetrahydroborate In 2-methyltetrahydrofuran for 4h; Cooling with ice; | 70% |
With lithium tri-t-butoxyaluminum hydride In diethyl ether at 0℃; for 4h; diastereoselective reaction; | 39 g |
1-(4-(pyridin-2-yl)benzyl)hydrazine
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 14.43 g / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 / 1.5 h / 20 °C 2: 25 percent / propan-2-ol / 24 h / Heating 3: HCl / tetrahydrofuran; H2O / 5 h / 50 °C 4: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 View Scheme |
(S)-{2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 25 percent / propan-2-ol / 24 h / Heating 2: HCl / tetrahydrofuran; H2O / 5 h / 50 °C 3: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium iodide / acetonitrile / 0.25 h / 20 °C 1.2: 0.25 h / 20 °C 2.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C View Scheme |
{(1S,2S)-1-benzyl-2-hydroxy-3-[N'-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyryl)-N-(4-pyridin-2-yl-benzyl)-hydrazino]-propyl}-carbamic acid tert-butyl ester
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HCl / tetrahydrofuran; H2O / 5 h / 50 °C 2: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 View Scheme |
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 25 percent / propan-2-ol / 24 h / Heating 2: HCl / tetrahydrofuran; H2O / 5 h / 50 °C 3: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 View Scheme | |
Multi-step reaction with 3 steps 1: isopropyl alcohol / 24 h / Inert atmosphere; Reflux; Large scale 2: hydrogenchloride / tetrahydrofuran / 3 h / 22 - 55 °C / Large scale 3: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 - 25 °C / Large scale View Scheme |
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 14.43 g / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 / 1.5 h / 20 °C 2: 25 percent / propan-2-ol / 24 h / Heating 3: HCl / tetrahydrofuran; H2O / 5 h / 50 °C 4: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 View Scheme | |
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / -25 - 20 °C 2.1: sodium iodide / acetonitrile / 0.25 h / 20 °C 2.2: 0.25 h / 20 °C 3.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / ethyl acetate / 0.5 h 1.2: 16 h 2.1: hydrogenchloride / tetrahydrofuran / 2 h / 20 °C 3.1: triethylamine / ethanol / 1 h / 20 °C / Inert atmosphere 3.2: 4 h / Inert atmosphere; Reflux 4.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr 5.1: sodium iodide / acetonitrile / 0.25 h / 20 °C 5.2: 0.25 h / 20 °C 6.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 - 25 °C 2: dipotassium hydrogenphosphate / water / 5 - 40 °C View Scheme |
N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: HCl / tetrahydrofuran; H2O / 3 h / 50 °C 2: 14.43 g / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 / 1.5 h / 20 °C 3: 25 percent / propan-2-ol / 24 h / Heating 4: HCl / tetrahydrofuran; H2O / 5 h / 50 °C 5: 95 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH2Cl2 View Scheme | |
Multi-step reaction with 3 steps 1: 69 percent / propan-2-ol / 16 h / Heating 2: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C 3: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight View Scheme | |
Multi-step reaction with 3 steps 1: isopropyl alcohol / 24 h / Inert atmosphere; Reflux; Large scale 2: hydrogenchloride / tetrahydrofuran / 3 h / 22 - 55 °C / Large scale 3: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 - 25 °C / Large scale View Scheme |
2-bromo-pyridine
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 1.) Mg, I2, 2.) <1,3-bis(diphenylphosphino)propane>nickel(II) chloride, diisobutylaluminum hydride, 3.) aq. HCl 2: 93 percent / ethanol / 4 h / Heating 3: 89 percent / H2 / 10percent Pd/C / methanol 4: 69 percent / propan-2-ol / 16 h / Heating 5: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C 6: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight View Scheme | |
Multi-step reaction with 6 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 20 h / 76 °C / Inert atmosphere 2: toluene; isopropyl alcohol / 2 h / 80 - 85 °C / Inert atmosphere; Large scale 3: palladium 10% on activated carbon; sodium formate / water; ethanol / 1.5 h / 57 °C 4: isopropyl alcohol / 24 h / Inert atmosphere; Reflux; Large scale 5: hydrogenchloride / tetrahydrofuran / 3 h / 22 - 55 °C / Large scale 6: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 - 25 °C / Large scale View Scheme |
2-(4-formylphenyl)pyridine
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 93 percent / ethanol / 4 h / Heating 2: 89 percent / H2 / 10percent Pd/C / methanol 3: 69 percent / propan-2-ol / 16 h / Heating 4: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C 5: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight View Scheme | |
Multi-step reaction with 5 steps 1: toluene; isopropyl alcohol / 2 h / 80 - 85 °C / Inert atmosphere; Large scale 2: palladium 10% on activated carbon; sodium formate / water; ethanol / 1.5 h / 57 °C 3: isopropyl alcohol / 24 h / Inert atmosphere; Reflux; Large scale 4: hydrogenchloride / tetrahydrofuran / 3 h / 22 - 55 °C / Large scale 5: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 - 25 °C / Large scale View Scheme | |
Multi-step reaction with 4 steps 1.1: triethylamine / ethanol / 1 h / 20 °C / Inert atmosphere 1.2: 4 h / Inert atmosphere; Reflux 2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr 3.1: sodium iodide / acetonitrile / 0.25 h / 20 °C 3.2: 0.25 h / 20 °C 4.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C View Scheme |
L-tert-Leucine
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / 2N aq. NaOH / dioxane / 18 h / 60 °C 2: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 18 h / 60 °C 1.2: 25 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 25 - 30 °C 2.2: 3 h View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydroxide / tetrahydrofuran / 60 °C 2.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / -25 - 20 °C 3.1: sodium iodide / acetonitrile / 0.25 h / 20 °C 3.2: 0.25 h / 20 °C 4.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: sodium hydroxide / tetrahydrofuran / 60 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / ethyl acetate / 0.5 h 2.2: 16 h 3.1: hydrogenchloride / tetrahydrofuran / 2 h / 20 °C 4.1: triethylamine / ethanol / 1 h / 20 °C / Inert atmosphere 4.2: 4 h / Inert atmosphere; Reflux 5.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr 6.1: sodium iodide / acetonitrile / 0.25 h / 20 °C 6.2: 0.25 h / 20 °C 7.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C View Scheme |
1,1-dimethoxy-1-(4-bromophenyl)methane
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 1.) Mg, I2, 2.) <1,3-bis(diphenylphosphino)propane>nickel(II) chloride, diisobutylaluminum hydride, 3.) aq. HCl 2: 93 percent / ethanol / 4 h / Heating 3: 89 percent / H2 / 10percent Pd/C / methanol 4: 69 percent / propan-2-ol / 16 h / Heating 5: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C 6: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight View Scheme | |
Multi-step reaction with 6 steps 1.1: magnesium; iodine / tetrahydrofuran / 2 h / 20 °C / Heating 1.2: 2.25 h / 20 °C 2.1: hydrogenchloride / water; tetrahydrofuran / Cooling with ice 3.1: triethylamine / ethanol / 1 h / 20 °C / Inert atmosphere 3.2: 4 h / Inert atmosphere; Reflux 4.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr 5.1: sodium iodide / acetonitrile / 0.25 h / 20 °C 5.2: 0.25 h / 20 °C 6.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C View Scheme |
N-(tert-butoxycarbonyl)-N'-[4-(pyridin-2-yl)phenylmethylidene]hydrazine
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 89 percent / H2 / 10percent Pd/C / methanol 2: 69 percent / propan-2-ol / 16 h / Heating 3: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C 4: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight View Scheme |
1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 100 percent / aq. HCl / tetrahydrofuran / 4 h / 50 °C 2: 1.) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, N-ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / tetrahydrofuran / 3 h / 22 - 55 °C / Large scale 2: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 - 25 °C / Large scale View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; water / 0.5 - 40 °C 2: dipotassium hydrogenphosphate / water / 5 - 40 °C View Scheme |
atazanavir
Conditions | Yield |
---|---|
In ethanol; dichloromethane; water; ethyl acetate | |
In ethanol; dichloromethane; water; ethyl acetate |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 2.5h; |
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
atazanavir
Conditions | Yield |
---|---|
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25 - 30℃; Stage #2: (2S,3S)-3-amino-4-phenyl-1-(1-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-ol hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane; water for 3h; Product distribution / selectivity; |
methyl [(2S)-3,3-dimethyl-1-({(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: water / 60 - 65 °C 2.1: hydrogenchloride; water / tetrahydrofuran / 6 h / 60 - 65 °C 3.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3.5 h / -5 - 15 °C / Inert atmosphere 3.2: 16 h / 10 - 35 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: water; dichloromethane / 40 - 65 °C 2.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 60 - 65 °C 3.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / -5 - 20 °C / Inert atmosphere 3.2: 10 - 15 °C 3.3: 10 - 35 °C View Scheme |
1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride; water / tetrahydrofuran / 6 h / 60 - 65 °C 2.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3.5 h / -5 - 15 °C / Inert atmosphere 2.2: 16 h / 10 - 35 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 60 - 65 °C 2.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / -5 - 20 °C / Inert atmosphere 2.2: 10 - 15 °C 2.3: 10 - 35 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With thionyl chloride; benzotriazol-1-ol; triethylamine In dichloromethane at -5 - 15℃; for 3.5h; Inert atmosphere; Stage #2: 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane dihydrochioride With dipotassium hydrogenphosphate In dichloromethane; water at 10 - 35℃; for 16h; | |
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With thionyl chloride; benzotriazol-1-ol; triethylamine In dichloromethane at -5 - 20℃; Inert atmosphere; Stage #2: With dipotassium hydrogenphosphate In dichloromethane; water at 10 - 15℃; Stage #3: 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane dihydrochioride In dichloromethane; water at 10 - 35℃; |
(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: hydrogenchloride; water / tetrahydrofuran / 4 h / 50 - 55 °C 2.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere 2.2: 12 h / 30 - 35 °C 3.1: tetrabutylammomium bromide; potassium hydroxide / dichloromethane; water / 3 h / 0 - 10 °C 4.1: water / 60 - 65 °C 5.1: hydrogenchloride; water / tetrahydrofuran / 6 h / 60 - 65 °C 6.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3.5 h / -5 - 15 °C / Inert atmosphere 6.2: 16 h / 10 - 35 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: hydrogenchloride / tetrahydrofuran; water / 4 h / 50 - 55 °C 2.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere 2.2: 10 - 15 °C 2.3: 12 h / 30 - 35 °C 3.1: tetrabutylammomium bromide; potassium hydroxide / water; dichloromethane / 3 h / 0 - 10 °C 4.1: water; dichloromethane / 40 - 65 °C 5.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 60 - 65 °C 6.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / -5 - 20 °C / Inert atmosphere 6.2: 10 - 15 °C 6.3: 10 - 35 °C View Scheme |
(2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere 1.2: 12 h / 30 - 35 °C 2.1: tetrabutylammomium bromide; potassium hydroxide / dichloromethane; water / 3 h / 0 - 10 °C 3.1: water / 60 - 65 °C 4.1: hydrogenchloride; water / tetrahydrofuran / 6 h / 60 - 65 °C 5.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3.5 h / -5 - 15 °C / Inert atmosphere 5.2: 16 h / 10 - 35 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere 1.2: 10 - 15 °C 1.3: 12 h / 30 - 35 °C 2.1: tetrabutylammomium bromide; potassium hydroxide / water; dichloromethane / 3 h / 0 - 10 °C 3.1: water; dichloromethane / 40 - 65 °C 4.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 60 - 65 °C 5.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / -5 - 20 °C / Inert atmosphere 5.2: 10 - 15 °C 5.3: 10 - 35 °C View Scheme |
atazanavir
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: tetrabutylammomium bromide; potassium hydroxide / dichloromethane; water / 3 h / 0 - 10 °C 2.1: water / 60 - 65 °C 3.1: hydrogenchloride; water / tetrahydrofuran / 6 h / 60 - 65 °C 4.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / 3.5 h / -5 - 15 °C / Inert atmosphere 4.2: 16 h / 10 - 35 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: tetrabutylammomium bromide; potassium hydroxide / water; dichloromethane / 3 h / 0 - 10 °C 2.1: water; dichloromethane / 40 - 65 °C 3.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 60 - 65 °C 4.1: benzotriazol-1-ol; triethylamine; thionyl chloride / dichloromethane / -5 - 20 °C / Inert atmosphere 4.2: 10 - 15 °C 4.3: 10 - 35 °C View Scheme |
atazanavir
Conditions | Yield |
---|---|
With sulfuric acid In acetone at 0 - 50℃; for 2h; | 95% |
With sulfuric acid In ethanol at 20 - 30℃; Temperature; Concentration; | 95.2% |
With sulfuric acid; pyrographite In 1,2-dimethoxyethane; dimethyl sulfoxide at 35℃; Solvent; Inert atmosphere; | 94% |
atazanavir
Conditions | Yield |
---|---|
With hydrogen bromide In acetone at 20 - 55℃; for 2.5h; Concentration; Solvent; Temperature; | 92.3% |
N-benzyl-N-(tert-butoxycarbonyl)glycine
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 35℃; for 72h; Inert atmosphere; | 80% |
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 35℃; for 72h; Inert atmosphere; Glovebox; | 146.1 mg |
dimethyl sulfoxide
atazanavir
Conditions | Yield |
---|---|
With acetic anhydride; acetic acid at 20℃; for 48h; Inert atmosphere; | 79% |
BOC-glycine
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 14h; Inert atmosphere; | 76% |
atazanavir
Conditions | Yield |
---|---|
Stage #1: atazanavir In ethanol at 25 - 30℃; for 0.5h; Stage #2: With sulfuric acid In ethanol; n-heptane; acetone at 15 - 40℃; Temperature; | 75.5% |
t-Boc-L-valine
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere; | 74.1% |
N-tert-butoxycarbonyl-L-phenylalanine
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere; | 74% |
Boc-D-Phe-OH
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere; | 71.2% |
carbonochloridic acid 1-chloro-ethyl ester
atazanavir
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 3h; | 70% |
(S)-2-(2-N-tert-butoxycarbonylamino)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-propanoic acid
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere; | 67.7% |
carbonochloridic acid, chloromethyl ester
atazanavir
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 3h; | 66% |
Conditions | Yield |
---|---|
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 35℃; for 72h; Reagent/catalyst; Inert atmosphere; | 65% |
L-N-Boc-Ala
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere; | 64.4% |
N-(tert-butoxycarbonyl)sarcosine
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere; | 64% |
Dibenzyl N,N-diisopropylphosphoramidite
atazanavir
Conditions | Yield |
---|---|
Stage #1: Dibenzyl N,N-diisopropylphosphoramidite; atazanavir With 1H-tetrazole In acetonitrile at 20℃; for 8h; Inert atmosphere; Stage #2: With dihydrogen peroxide In water; acetonitrile at 0℃; for 0.166667h; | 62.4% |
Boc-(R)-Ala
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere; | 60.3% |
Boc-Phe(p-F)
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere; | 58.1% |
dimethylaminoacetic acid
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere; | 57.1% |
Conditions | Yield |
---|---|
With pentamethylcyclopentadienyl(benzene)cobalt(III) hexafluorophosphate; potassium carbonate; silver carbonate In 2-methyltetrahydrofuran at 100℃; for 16h; Inert atmosphere; Sealed tube; | 55% |
Boc-Trp-OH
atazanavir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 14h; Inert atmosphere; | 51.6% |
The Atazanavir , with cas registry number of 198904-31-3, is a kind of categories of API; Inhibitors; All Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. Its IUPAC name is called methyl N-[(2S)-1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-4-phenylbutyl]-2-[(4-pyridin-2-ylphenyl)methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate . Its appearance is crystalline solid. Itt is used as a drug to treat infection of human immunodeficiency virus.
Physical properties about this chemical are: (1) ACD/LogP: 5.20 ; (2) # of Rule of 5 Violations: 4 ; (3) ACD/LogD (pH 5.5): 5.14 ; (4) ACD/LogD (pH 7.4): 5.2 ; (5) ACD/BCF (pH 5.5): 4599.86 ; (6) ACD/BCF (pH 7.4): 5235.96 ; (7) ACD/KOC (pH 5.5): 14024.21 ; (8) ACD/KOC (pH 7.4): 15963.56 ; (9) #H bond acceptors: 13 ; (10) #H bond donors: 5 ; (11) #Freely Rotating Bonds: 19 ; (12) Polar Surface Area: 125.06 Å2 ; (13) Index of Refraction: 1.562 ; (14) Molar Refractivity: 194 cm3 ; (15) Molar Volume: 597.9 cm3 ; (16) Surface Tension: 47.9 dyne/cm ; (17) Density: 1.178 g/cm3.
You can still convert the following datas into molecular structure:
(1)SMILES:O=C(OC)N[C@H](C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)Cc3ccc(c2ncccc2)cc3)C(C)(C)C;
(2)InChI:InChI=1/C38H52N6O7/c1-37(2,3)31(41-35(48)50-7)33(46)40-29(22-25-14-10-9-11-15-25)30(45)24-44(43-34(47)32(38(4,5)6)42-36(49)51-8)23-26-17-19-27(20-18-26)28-16-12-13-21-39-28/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47)/t29-,30-,31+,32+/m0/s1;
(3)InChIKey:AXRYRYVKAWYZBR-GASGPIRDBE
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