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179324-69-7

Basic Information
CAS No.: 179324-69-7
Name: Bortezomib
Article Data: 22
Cas Database
Molecular Structure:
Molecular Structure of 179324-69-7 (Bortezomib)
Formula: C19H25BN4O4
Molecular Weight: 384.243
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);
EINECS: 605-854-3
Density: 1.214 g/cm3
Melting Point: 122-124 °C
Boiling Point: N/A
Flash Point: N/A
Solubility: N/A
Appearance: yellow solid
Hazard Symbols: N/A
Risk Codes: 23/24/25-48/23/24/25
Safety: 9-27-36/37-45-60
Transport Information: N/A
PSA: 124.44000
LogP: 1.56230
Synthetic route
13061-96-6

dihydroxy-methyl-borane

1029701-48-1

bortezomib pinacol ester

Conditions
ConditionsYield
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

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

C24H33BN4O4

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

C26H37BN4O4

Conditions
ConditionsYield
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

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

C25H35BN4O4

Conditions
ConditionsYield
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

Conditions
ConditionsYield
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

Conditions
ConditionsYield
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

Conditions
ConditionsYield
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%
98-97-5

2-pyrazylcarboxylic acid

C23H27BNO5Pol

35661-40-6

N-Fmoc L-Phe

Conditions
ConditionsYield
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%
Downstream Products
114457-94-2
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Chemistry


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

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.

Uses

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

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.