Bortezomib supplier | CasNO.179324-69-7

Name
Bortezomib
EINECS 605-854-3
CAS No. 179324-69-7
Article Data22
CAS DataBase
Density 1.214 g/cm³
Solubility
Melting Point 122-124 °C
Formula C₁₉H₂₅BN₄O₄
Boiling Point
Molecular Weight 384.243
Flash Point
Transport Information
Appearance yellow solid
Safety 9-27-36/37-45-60
Risk Codes 23/24/25-48/23/24/25
Molecular Structure
Hazard Symbols
Synonyms Pyz-Phe-boroLeu;Boronic acid, [(1(R)-3-methyl-1-[[(2S)-1-oxo-3-phenyl-2-[(pyrazinylcarbonyl)amino]propyl]amino]butyl]-;Boronic acid, [1-[[1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl) amino]propyl]amino]-3-methylbutyl]-, L-(S)-;[(1R)-3-methyl-1-[[(2S)-3-phenyl-2-(pyrazine-2-carbonylamino)propanoyl]amino]butyl]boronic acid;PS 341 (pharmaceutical);
PSA 124.44000
LogP 1.56230

Synthetic route

: 13061-96-6
dihydroxy-methyl-borane

: 1029701-48-1
bortezomib pinacol ester

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone at 20℃;	94%

: 205393-22-2
N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide

: 13061-96-6
dihydroxy-methyl-borane

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone at 20℃; for 40h;	92%

: C24H33BN4O4

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride; 2-methyl-propan-1-ol In methanol; pentane at 0 - 20℃; for 12h; Large scale;	86%

: C26H37BN4O4

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride; 2-methyl-propan-1-ol In methanol; pentane at 0 - 20℃; for 12h; Large scale;	86%

: (2S)-N-[(1R)-1-(1,3,6,2-dioxazaborocan-2-yl)-3-methylbutyl]-3-phenyl-2-(pyrazin-2-ylformamido)propanamide

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 20℃;	82.3%

: C25H35BN4O4

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride; 2-methyl-propan-1-ol In methanol; pentane at 0 - 20℃; for 12h; Large scale;	82%

: 205393-22-2
N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride; Dihydroxy-isobutyl-boran In water at 20℃; Solvent; Temperature;	77%
With hydrogenchloride; Dihydroxy-isobutyl-boran In methanol; n-heptane; water at 25 - 30℃; for 1 - 2h; Product distribution / selectivity;	70%
With hydrogenchloride; Dihydroxy-isobutyl-boran; water In methanol; hexane at 20℃; for 18h;	56.4%

: 84110-40-7
Dihydroxy-isobutyl-boran

: C29H39BN4O4

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride In methanol; n-heptane; water at 0 - 25℃; for 2h;	71.5%

: 98-97-5
2-pyrazylcarboxylic acid

: 19461-04-2
N-benzyl-L-phenylalanine

: (R)-1-amino-3-methylbutylboronic acid pinanediol ester hydrochloride

: 179324-69-7
velcade

Conditions

Conditions	Yield
Stage #1: N-benzyl-L-phenylalanine; (R)-1-amino-3-methylbutylboronic acid pinanediol ester hydrochloride With 4-methyl-morpholine; N-ethyl-N,N-diisopropylamine; isobutyryl chloride In tetrahydrofuran at 55℃; for 2h; pH=10; Inert atmosphere; Stage #2: With palladium on activated charcoal; hydrogen In tetrahydrofuran at 68℃; under 4560.31 Torr; for 2h; Stage #3: 2-pyrazylcarboxylic acid Concentration; Temperature; Solvent; pH-value; Pressure; Further stages;	67%

Yield

Stage #1: N-benzyl-L-phenylalanine; (R)-1-amino-3-methylbutylboronic acid pinanediol ester hydrochloride With 4-methyl-morpholine; N-ethyl-N,N-diisopropylamine; isobutyryl chloride In tetrahydrofuran at 55℃; for 2h; pH=10; Inert atmosphere;
Stage #2: With palladium on activated charcoal; hydrogen In tetrahydrofuran at 68℃; under 4560.31 Torr; for 2h;
Stage #3: 2-pyrazylcarboxylic acid Concentration; Temperature; Solvent; pH-value; Pressure; Further stages;

67%

...Expand

: 98-97-5
2-pyrazylcarboxylic acid

: C23H27BNO5Pol

: 35661-40-6
N-Fmoc L-Phe

: 179324-69-7
velcade

Conditions

Conditions	Yield
Stage #1: C23H27BNO5Pol With piperidine In N,N-dimethyl-formamide for 0.333333h; 1-glycerol polystyrene resin; Stage #2: N-Fmoc L-Phe With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 2h; 1-glycerol polystyrene resin; Stage #3: 2-pyrazylcarboxylic acid Further stages;	54%

...Expand

: (S)-N-(1-(isopentylamino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide

: 98-80-6
phenylboronic acid

: 179324-69-7
velcade

Conditions

Conditions	Yield
Stage #1: (S)-N-(1-(isopentylamino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide With [Rh(OH)(cod)]2; 4-((2'-((triisopropylsilyl)oxy)-[1,1'-binaphthalen]-2-yl)oxy)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine; bis(pinacol)diborane In acetonitrile at 80℃; for 36h; Inert atmosphere; Sealed tube; Stage #2: phenylboronic acid With hydrogenchloride In methanol; water; pentane at 20℃; for 12h; Inert atmosphere; stereoselective reaction;	53%

Yield

Stage #1: (S)-N-(1-(isopentylamino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide With [Rh(OH)(cod)]2; 4-((2'-((triisopropylsilyl)oxy)-[1,1'-binaphthalen]-2-yl)oxy)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine; bis(pinacol)diborane In acetonitrile at 80℃; for 36h; Inert atmosphere; Sealed tube;
Stage #2: phenylboronic acid With hydrogenchloride In methanol; water; pentane at 20℃; for 12h; Inert atmosphere; stereoselective reaction;

53%

: 1029701-48-1
bortezomib pinacol ester

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride; 2-methyl-propan-1-ol In methanol; pentane at 0 - 20℃; for 12h;	52%
With hydrogenchloride In methanol; pentane for 20h;	93.4 mg
Stage #1: bortezomib pinacol ester With hydrogenchloride; Dihydroxy-isobutyl-boran In methanol; n-heptane; water at 20℃; Stage #2: With sodium hydroxide In water
With hydrogenchloride; Dihydroxy-isobutyl-boran

: 98-97-5
2-pyrazylcarboxylic acid

: 1029701-41-4
(CH3)2CHCH2CH(BO2C2(CH3)4)NHCOCH(CH2C6H5)NH3(1+)*Cl(1-)=(CH3)2CHCH2CH(BO2C2(CH3)4)NHCOCH(CH2C6H5)NH3Cl

: 179324-69-7
velcade

Conditions

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In not given 1. (2-pyrazine)CO2H, TBTU, i-Pr2EtN, 0°C - room temp.; 2. i-BuB(OH)2, pentane, MeOH, 1 N HCl;

: (2S)-N-[1-(1,3,6,2-dioxazaborocan-2-yl)-3-methylbutyl]-3-phenyl-2-(pyrazin-2-ylformamido)propanamide

A: 1132709-14-8
[(1S)-1-[[(2S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]-1-oxopropyl]amino]-3-methylbutyl]boronic acid

B: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 20℃;

: C32H43BN2O5

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen; palladium 10% on activated carbon / N,N-dimethyl-formamide 2: N-ethyl-N,N-diisopropylamine / dichloromethane 3: methanol / Acidic conditions View Scheme

: 789472-91-9
N-{(1S)-3-methyl-1-[(3aS,4S,6S,7aS)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}phenylalanine amide

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane 2: methanol / Acidic conditions View Scheme

: 1161-13-3
N-Cbz-L-Phe

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane 2: hydrogen; palladium 10% on activated carbon / N,N-dimethyl-formamide 3: N-ethyl-N,N-diisopropylamine / dichloromethane 4: methanol / Acidic conditions View Scheme

: 98-97-5
2-pyrazylcarboxylic acid

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: thionyl chloride / toluene / 75 °C 2.1: sodium carbonate / toluene; water / 10 - 25 °C 3.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / -40 - -11 °C 4.1: hydrogenchloride; Dihydroxy-isobutyl-boran / water; methanol; n-heptane / 20 °C 4.2: 20 °C 5.1: hydrogenchloride / water; methanol / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 0.67 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: sodium hydroxide / water; acetone / 2 h / 0 °C 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / -10 - -5 °C 4.1: hydrogenchloride / water; acetone / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 0.67 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: sodium hydroxide / water; acetone / 2 h / 0 °C 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / -10 - -5 °C 4.1: hydrogenchloride / water; acetone / 40 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride 2: hydrogenchloride; Dihydroxy-isobutyl-boran View Scheme
Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C 2: sodium hydroxide / methanol; water / 20 °C 3: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C 4: Dihydroxy-isobutyl-boran; hydrogenchloride / water; methanol; ethyl acetate View Scheme

: (3aS,4S,6S,7aR)-2-(1-chloro-3-methylbutyl)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: hexane / -70 - 20 °C / Large scale 2: di-isopropyl ether / 2 h / -10 - 0 °C / Large scale 3: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale 4: hydrogenchloride / toluene / 1 h / 0 °C / Large scale 5: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale 6: hydrogenchloride; Dihydroxy-isobutyl-boran / hexane; 1,1,1-trideuteromethanol; water / 0 - 20 °C / Large scale View Scheme

Yield

Multi-step reaction with 6 steps
1: hexane / -70 - 20 °C / Large scale
2: di-isopropyl ether / 2 h / -10 - 0 °C / Large scale
3: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale
4: hydrogenchloride / toluene / 1 h / 0 °C / Large scale
5: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale
6: hydrogenchloride; Dihydroxy-isobutyl-boran / hexane; 1,1,1-trideuteromethanol; water / 0 - 20 °C / Large scale
View Scheme

: 514820-48-5
1,1,1-trimethyl-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}-N-(trimethylsilyl)silanamine

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: di-isopropyl ether / 2 h / -10 - 0 °C / Large scale 2: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale 3: hydrogenchloride / toluene / 1 h / 0 °C / Large scale 4: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale 5: hydrogenchloride; Dihydroxy-isobutyl-boran / hexane; 1,1,1-trideuteromethanol; water / 0 - 20 °C / Large scale View Scheme
Multi-step reaction with 4 steps 1.1: hydrogenchloride / tert-butyl methyl ether / -40 - 20 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / -40 - -11 °C 3.1: hydrogenchloride; Dihydroxy-isobutyl-boran / water; methanol; n-heptane / 20 °C 3.2: 20 °C 4.1: hydrogenchloride / water; methanol / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: di-isopropyl ether / 2 h / -10 - 0 °C / Large scale
2: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale
3: hydrogenchloride / toluene / 1 h / 0 °C / Large scale
4: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale
5: hydrogenchloride; Dihydroxy-isobutyl-boran / hexane; 1,1,1-trideuteromethanol; water / 0 - 20 °C / Large scale
View Scheme

Multi-step reaction with 4 steps
1.1: hydrogenchloride / tert-butyl methyl ether / -40 - 20 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / -40 - -11 °C
3.1: hydrogenchloride; Dihydroxy-isobutyl-boran / water; methanol; n-heptane / 20 °C
3.2: 20 °C
4.1: hydrogenchloride / water; methanol / 20 °C
View Scheme

: (aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale 2: hydrogenchloride / toluene / 1 h / 0 °C / Large scale 3: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale 4: hydrogenchloride; Dihydroxy-isobutyl-boran / hexane; 1,1,1-trideuteromethanol; water / 0 - 20 °C / Large scale View Scheme
Multi-step reaction with 3 steps 1.1: dichloromethane / 0.08 h / 0 °C / Inert atmosphere 1.2: 1 h / -3 - 2 °C 1.3: 0.25 h / 15 - 27 °C 2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / toluene / 0.17 h / Inert atmosphere 2.2: 3 h / 25 °C 3.1: hydrogenchloride; Dihydroxy-isobutyl-boran / methanol; n-heptane / 12 h / 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale
2: hydrogenchloride / toluene / 1 h / 0 °C / Large scale
3: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale
4: hydrogenchloride; Dihydroxy-isobutyl-boran / hexane; 1,1,1-trideuteromethanol; water / 0 - 20 °C / Large scale
View Scheme

Multi-step reaction with 3 steps
1.1: dichloromethane / 0.08 h / 0 °C / Inert atmosphere
1.2: 1 h / -3 - 2 °C
1.3: 0.25 h / 15 - 27 °C
2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / toluene / 0.17 h / Inert atmosphere
2.2: 3 h / 25 °C
3.1: hydrogenchloride; Dihydroxy-isobutyl-boran / methanol; n-heptane / 12 h / 20 °C
View Scheme

: tert-butyl [1-({3-methyl-1-[(3aS,4S,6S)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-1-oxo-3-phenylpropan-2-yl]carbamate

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / toluene / 1 h / 0 °C / Large scale 2: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale 3: hydrogenchloride; Dihydroxy-isobutyl-boran / hexane; 1,1,1-trideuteromethanol; water / 0 - 20 °C / Large scale View Scheme

: N-{3-methyl-1-[(3aS,4S,6S)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}phenylalanine amide

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Large scale 2: hydrogenchloride; Dihydroxy-isobutyl-boran / hexane; 1,1,1-trideuteromethanol; water / 0 - 20 °C / Large scale View Scheme

: N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}-Nα-(pyrazin-2-ylcarbonyl)-L-phenylalaninamide

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride; Dihydroxy-isobutyl-boran In hexane; 1,1,1-trideuteromethanol; water at 0 - 20℃; Concentration; Temperature; Large scale;

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

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dichloromethane / 0.08 h / 0 °C / Inert atmosphere 1.2: 1 h / -3 - 2 °C 1.3: 0.25 h / 15 - 27 °C 2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / toluene / 0.17 h / Inert atmosphere 2.2: 3 h / 25 °C 3.1: hydrogenchloride; Dihydroxy-isobutyl-boran / methanol; n-heptane / 12 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: N-isopropylethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / acetonitrile / 2 h / -10 - 5 °C 2: dichloromethane / 25 - 35 °C 3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / acetonitrile / 0 - 10 °C 4: Dihydroxy-isobutyl-boran; hydrogenchloride / water / 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1: N-isopropylethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / acetonitrile / 2 h / -10 - 5 °C
2: dichloromethane / 25 - 35 °C
3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / acetonitrile / 0 - 10 °C
4: Dihydroxy-isobutyl-boran; hydrogenchloride / water / 20 °C
View Scheme

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / 0.33 h / 20 °C / Inert atmosphere 1.2: 4 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride; Dihydroxy-isobutyl-boran / n-heptane; water; methanol / 1.5 h / 20 - 30 °C View Scheme
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / -40 - -11 °C 2.1: hydrogenchloride; Dihydroxy-isobutyl-boran / water; methanol; n-heptane / 20 °C 2.2: 20 °C 3.1: hydrogenchloride / water; methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / -10 - -5 °C 2: hydrogenchloride / water; acetone / 20 °C View Scheme

: (R)-boroleu-(+)-pinanediol trifluoroacetic acid

: 179324-69-7
velcade

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / 0.33 h / 20 °C / Inert atmosphere 1.2: 4 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride; Dihydroxy-isobutyl-boran / n-heptane; water; methanol / 1.5 h / 20 - 30 °C View Scheme

: N-((2S)-1-((3-methyl-1-((3aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)amino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride; Dihydroxy-isobutyl-boran In methanol; n-heptane; water at 20 - 30℃; for 1.5h;	4.2 g

: 67-64-1
acetone

: 98-80-6
phenylboronic acid

: 179324-69-7
velcade

Conditions

Conditions	Yield
With hydrogenchloride In hexane; acetonitrile

: 179324-69-7
velcade

: 289472-78-2
Pyrazine-2-carboxylic acid [(S)-1-((R)-1-hydroxy-3-methyl-butylcarbamoyl)-2-phenyl-ethyl]-amide

Conditions

Conditions	Yield
With dihydrogen peroxide In ethanol; water at 20℃; for 1h; Oxidation; hydrolysis;	100%
With hydrogenchloride; oxygen In ethanol; water at 25℃; for 336h; pH=2.8; Kinetics; Product distribution; Further Variations:; with/without ascorbic acid; Oxidation; hydrolysis;
With oxygen In ethanol; water at 25℃; for 5844h; pH=6.9; Kinetics; Product distribution; Further Variations:; with/without EDTA; Oxidation; hydrolysis;

: C16H29N3O4

: 179324-69-7
velcade

: C35H50BN7O6

Conditions

Conditions	Yield
In chloroform-d1 at 45℃;	95%

: pinanediol

: 179324-69-7
velcade

: C29H39BN4O4

Conditions

Conditions	Yield
In toluene for 3h; Inert atmosphere; Reflux;	91.2%

: dopamine folic acid

: 179324-69-7
velcade

: C46H49BN12O9

Conditions

Conditions	Yield
In dimethyl sulfoxide at 25℃;	80%

: 179324-69-7
velcade

: 390800-88-1
bortezomib

Conditions

Conditions	Yield
In isopropyl alcohol; acetonitrile at 20℃; for 4h; Product distribution / selectivity;	76.9%

: 77-92-9
citric acid

: 179324-69-7
velcade

: 5-(carboxymethyl)-2-((R)-3-methyl-1-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)-6-oxo-1,3,2-dioxaborinane-4-carboxylic acid

Conditions

Conditions	Yield
In ethyl acetate at 20 - 74℃; for 3h;	71.1%

: C14H29N3O6

: 179324-69-7
velcade

: C33H50BN7O8

Conditions

Conditions	Yield
In chloroform-d1	70%

: 179324-69-7
velcade

A: Pyrazine-2-carboxylic acid ((S)-1-carbamoyl-2-phenyl-ethyl)-amide

B: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
With sodium hydroxide; oxygen In dimethyl sulfoxide at 70℃; for 250h; pH=12.0; Kinetics; Product distribution; Oxidation; hydrolysis;
With sodium hydroxide; oxygen at 70℃; for 48h; pH=12; Oxidation; hydrolysis;

: 179324-69-7
velcade

A: Pyrazine-2-carboxylic acid ((S)-1-carbamoyl-2-phenyl-ethyl)-amide

B: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

C: 289472-78-2
Pyrazine-2-carboxylic acid [(S)-1-((R)-1-hydroxy-3-methyl-butylcarbamoyl)-2-phenyl-ethyl]-amide

D: Pyrazine-2-carboxylic acid [(S)-1-((S)-1-hydroxy-3-methyl-butylcarbamoyl)-2-phenyl-ethyl]-amide

Conditions

Conditions	Yield
With dihydrogen peroxide In water at 20℃; for 1h; Kinetics; Product distribution; Further Variations:; Solvents; Oxidation; hydrolysis;

...Expand

: 179324-69-7
velcade

: 114457-94-2
(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions

Conditions	Yield
With hydrogenchloride; oxygen In dimethyl sulfoxide at 70℃; for 250h; pH=1.0; Kinetics; Product distribution; Oxidation; hydrolysis;
With hydrogenchloride; oxygen at 70℃; for 120h; pH=1.0; Oxidation; hydrolysis;

: 62-31-7
dopamine hydrochloride

: 179324-69-7
velcade

: C27H33BN5O5(1-)*H(1+)

Conditions

Conditions	Yield
With sodium dihydrogenphosphate; sodium hydroxide In dimethylsulfoxide-d6; water-d2 for 1h; pH=7.4;

Bortezomib Chemical Properties

IUPAC Name: [(1R)-3-Methyl-1-[[(2S)-3-phenyl-2-(pyrazine-2-carbonylamino)propanoyl] amino]butyl]boronic acid
Molecular Formula: C₁₉H₂₅BN₄O₄
Molecular Weight: 384.24 g/mol
SMILES: O=C(N[C@@H](C(=O)N[C@@H](B(O)O)CC(C)C)Cc1ccccc1)c2nccnc2 Copy
InChI: InChI=1/C19H25BN4O4/c1-13(2)10-17(20(27)28)24-18(25)15(11-14-6-4-3-5-7-14)23-19(26)16-12-21-8-9-22-16/h3-9,12-13,15,17,27-28H,10-11H2,1-2H3,(H,23,26)(H,24,25)/t15-,17-/m1/s1
Product Categories: Boron Derivatives; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals
Classification Code: Antineoplastic Agents; Enzyme Inhibitors; Protease Inhibitors; Treatment of multiple cancers, including multiple myeloma, chronic lymphocytic leukemia, non-Hodgkins lymphoma, and pancreatic, colon, lung, and prostate cancers [proteasome inhibitor]
Melting Point: 122-124 °C
Index of Refraction: 1.564
Molar Refractivity: 102.97 cm³
Molar Volume: 316.5 cm³
Surface Tension: 53.2 dyne/cm
Density of Bortezomib (CAS NO.179324-69-7): 1.214 g/cm³

Bortezomib History

In 1995, Bortezomib was first synthesized at a company called Myogenics, which soon changed its name to ProScript.
Bortezomib is the first proteasome inhibitor to be approved b the US FDA for multiple myeloma, a blood cancer. A reversible inhibitor of the 26S proteasome-a barrel-shaped multiprotein particle found in the nucleus and cytosol of all eukaryotic cel.It is approved in the U.S. for treating relapsed multiple myeloma and mantle cell lymphoma.

Bortezomib Uses

It is used as a medicine to treat some refractory disease, for example relapsed multiple myeloma and mantle cell lymphoma.

Bortezomib Specification

Bortezomib (CAS NO.179324-69-7), its Synonyms are ((1R)-3-Methyl-1-(((2S)-3-phenyl-2-((pyrazinylcarbonyl)amino)propanoyl)amino)butyl)boronic acid ; Boronic acid, ((1R)-3-methyl-1-(((2S)-1-oxo-3-phenyl-2-((pyrazinylcarbonyl)amino)propyl)amino)butyl)- ; N-((1S)-1-Benzyl-2-(((1R)-1-(dihydroxyboranyl)-3-methylbutyl)amino)-2-oxoethyl)pyrazinecarboxamide ; Velcade . It is yellow solid.

Product Name

Bortezomib

Synthetic route

Bortezomib Chemical Properties

Bortezomib History

Bortezomib Uses

Bortezomib Specification

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