Atazanavir supplier | CasNO.198904-31-3

Name
Atazanavir
EINECS 812-543-8
CAS No. 198904-31-3
Article Data20
CAS DataBase
Density 1.178 g/cm³
Solubility
Melting Point 207-209 °C
Formula C₃₈H₅₂N₆O₇
Boiling Point
Molecular Weight 704.867
Flash Point
Transport Information
Appearance crystalline solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,5,6,10,13-Pentaazatetradecanedioicacid,3,12-bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-,dimethyl ester, (3S,8S,9S,12S)- (9CI);BMS 232632;CGP 73547;Reyataz;
PSA 171.22000
LogP 5.77520

Synthetic route

: 869285-68-7
C14H18N4O4

: 1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride

: 198904-31-3
atazanavir

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In water at 5 - 40℃;	100%

: 857900-54-0
{(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

: 162537-11-3
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

: 198904-31-3
atazanavir

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane	95%

: 869285-68-7
C14H18N4O4

: 1-[4-(Pyridin-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane.3hydrochloride

: 198904-31-3
atazanavir

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In water at 5 - 40℃; for 1.5 - 2h;	95%

: 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-(5S)-2,5-diamino-6-phenyl-2-azahexane

: 162537-11-3
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

: 198904-31-3
atazanavir

Conditions

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%

: 857904-02-0
(S)-{2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester

: 1192510-20-5
methyl [(2S)-3,3-dimethyl-1-({(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate

: 198904-31-3
atazanavir

Conditions

Conditions	Yield
In dichloromethane for 64h; Silica gel;	87%
silica gel In dichloromethane for 64h;	87%
In isopropyl alcohol at 90℃; for 12h;

: 162537-11-3
(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 trihydrochloride

: 198904-31-3
atazanavir

Conditions

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;

: 162537-11-3
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

: 437713-06-9
1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane

: 198904-31-3
atazanavir

Conditions

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%

: 1-[4-(pyridin-2-yl)phenyl]-5(S)-2,5-bis{[N-(methoxycarbonyl)-L-tert-leucinyl]amino}-4-oxo-6-phenyl-2-azahexane

: 198904-31-3
atazanavir

Conditions

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

: 920757-34-2
1-(4-(pyridin-2-yl)benzyl)hydrazine

: 198904-31-3
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

: 857904-02-0
(S)-{2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester

: 198904-31-3
atazanavir

Conditions

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

: 857904-03-1
{(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

: 198904-31-3
atazanavir

Conditions

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

: 98760-08-8
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

: 198904-31-3
atazanavir

Conditions

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

: 162537-11-3
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

: 198904-31-3
atazanavir

Conditions

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

: 198904-85-7
N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

: 198904-31-3
atazanavir

Conditions

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

: 109-04-6
2-bromo-pyridine

: 198904-31-3
atazanavir

Conditions

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

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

: 127406-56-8
2-(4-formylphenyl)pyridine

: 198904-31-3
atazanavir

Conditions

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

: 20859-02-3
L-tert-Leucine

: 198904-31-3
atazanavir

Conditions

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

: 24856-58-4
1,1-dimethoxy-1-(4-bromophenyl)methane

: 198904-31-3
atazanavir

Conditions

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

Yield

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

: 857904-11-1
N-(tert-butoxycarbonyl)-N'-[4-(pyridin-2-yl)phenylmethylidene]hydrazine

: 198904-31-3
atazanavir

Conditions

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

: 198904-86-8
1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane

: 198904-31-3
atazanavir

Conditions

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

N-methoxycarbonyl-(L)-tert-leucine: N-methoxycarbonyl-(L)-tert-leucine

: 1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride

: 198904-31-3
atazanavir

Conditions

Conditions	Yield
In ethanol; dichloromethane; water; ethyl acetate
In ethanol; dichloromethane; water; ethyl acetate

: 1028634-76-5
C36H50N6O5

: 79-22-1
methyl chloroformate

: 198904-31-3
atazanavir

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 2.5h;

: (2S,3S)-3-amino-4-phenyl-1-(1-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-ol hydrochloride

: 162537-11-3
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

: 198904-31-3
atazanavir

Conditions

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;

: 1192510-20-5
methyl [(2S)-3,3-dimethyl-1-({(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate

: 198904-31-3
atazanavir

Conditions

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

: 198905-04-3
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

: 198904-31-3
atazanavir

Conditions

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

: 162537-11-3
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

: 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

: 198904-31-3
atazanavir

Conditions

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℃;

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℃;

: 162536-40-5
(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane

: 198904-31-3
atazanavir

Conditions

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

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

: 369362-96-9
(2S,3R)-2-amino-4-chloro-1-phenylbutan-3-ol hydrochloride

: 198904-31-3
atazanavir

Conditions

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

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

: methyl [(2S)-1-{[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]amino}-3,3-dimethyl-1-oxobutan-2-yl]carbamate

: 198904-31-3
atazanavir

Conditions

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

: 198904-31-3
atazanavir

: atazanavir sulphate

Conditions

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%

: 198904-31-3
atazanavir

: 1-[4-(pyridin-2-yl)phenyl]-(S)-2,5-bis{[N-(methoxycarbonyl)-L-tert-leucyl]amino}-4-(S)-hydroxy-6-phenyl-2-azahexane hydrobromide

Conditions

Conditions	Yield
With hydrogen bromide In acetone at 20 - 55℃; for 2.5h; Concentration; Solvent; Temperature;	92.3%

: 76315-01-0
N-benzyl-N-(tert-butoxycarbonyl)glycine

: 198904-31-3
atazanavir

: (5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-(benzyl(tert-butoxycarbonyl)amino)acetate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;	89%

: 556-96-7
5-bromo-1,3-xylene

: 198904-31-3
atazanavir

: C54H68N6O7

Conditions

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

: 67-68-5
dimethyl sulfoxide

: 198904-31-3
atazanavir

: methyl ((5S,8S,9S,14S)-8-benzyl-5-(tert-butyl)-15,15-dimethyl-9-((methylthio)methoxy)-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

Conditions

Conditions	Yield
With acetic anhydride; acetic acid at 20℃; for 48h; Inert atmosphere;	79%

: 4530-20-5
BOC-glycine

: 198904-31-3
atazanavir

: (5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-((tert-butoxycarbonyl)amino)acetate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 14h; Inert atmosphere;	76%

: 198904-31-3
atazanavir

: (3S,8S,9S,12S)-3,12-bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyrimidinyl)phenyl]methyl]-2,5,6,10,13-pentaazatetradecanedioate dimethyl sulfate

Conditions

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%

: 13734-41-3
t-Boc-L-valine

: 198904-31-3
atazanavir

: (2S,3S)-3-((S)-2-((methoxycarbonyl)amino)-3,3-dimethylbutanamido)-1-(2-((S)-2-((methoxycarbonyl)amino)-3,3-dimethylbutanoyl)-1-(4-(pyridin-2-yl)benzyl)hydrazinyl)-4-phenylbutan-2-yl (tert-butoxycarbonyl)-L-valinate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere;	74.1%

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 198904-31-3
atazanavir

: (5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;	74%

: 18942-49-9
Boc-D-Phe-OH

: 198904-31-3
atazanavir

: (5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (R)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;	71.2%

: 50893-53-3
carbonochloridic acid 1-chloro-ethyl ester

: 198904-31-3
atazanavir

: methyl ((5S,8S,9S,14S)-8-benzyl-5-(tert-butyl)-9-(((1-chloroethoxy)carbonyl)oxy)-15,15-dimethyl-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 3h;	70%

: 94732-15-7
(S)-2-(2-N-tert-butoxycarbonylamino)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-propanoic acid

: 198904-31-3
atazanavir

: (5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;	67.7%

: 22128-62-7
carbonochloridic acid, chloromethyl ester

: 198904-31-3
atazanavir

: methyl ((5S,8S,9S,14S)-8-benzyl-5-(tert-butyl)-9-(((chloromethoxy)carbonyl)oxy)-15,15-dimethyl-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 3h;	66%

: trametinib

: 198904-31-3
atazanavir

: C90H96F2N16O15

Conditions

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%

: 15761-38-3
L-N-Boc-Ala

: 198904-31-3
atazanavir

: (5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)propanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;	64.4%

: 13734-36-6
N-(tert-butoxycarbonyl)sarcosine

: 198904-31-3
atazanavir

: (5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-((tert-butoxycarbonyl)(methyl)amino)acetate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;	64%

: 108549-23-1
Dibenzyl N,N-diisopropylphosphoramidite

: 198904-31-3
atazanavir

: methyl ((5S,8S,9S,14S)-8-benzyl-9-((bis(benzyloxy)phosphoryl)-oxy)-5-(tert-butyl)-15,15-dimethyl-3,6,13-trioxo-11-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,11,12-tetraazahexadecan-14-yl)carbamate

Conditions

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%

: 3744-87-4, 7764-95-6, 15761-38-3
Boc-(R)-Ala

: 198904-31-3
atazanavir

: (5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (R)-2-((tert-butoxycarbonyl)amino)propanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;	60.3%

: 41153-30-4, 57292-45-2, 79561-25-4, 129101-25-3
Boc-Phe(p-F)

: 198904-31-3
atazanavir

: (5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-fluorophenyl)propanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;	58.1%

: 1118-68-9
dimethylaminoacetic acid

: 198904-31-3
atazanavir

: (5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl 2-(dimethylamino)acetate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;	57.1%

: 823-96-1
Trimethylboroxine

: 198904-31-3
atazanavir

: C40H56N6O7

Conditions

Conditions	Yield
With pentamethylcyclopentadienyl(benzene)cobalt(III) hexafluorophosphate; potassium carbonate; silver carbonate In 2-methyltetrahydrofuran at 100℃; for 16h; Inert atmosphere; Sealed tube;	55%

: 13139-14-5
Boc-Trp-OH

: 198904-31-3
atazanavir

: (5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 14h; Inert atmosphere;	51.6%

Atazanavir Specification

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

Product Name

Atazanavir

Synthetic route

Atazanavir Specification

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