CAS No.179324-69-7,Bortezomib Suppliers

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Basic Information

Molecular Structure:
CAS No.:	179324-69-7
Name:	Bortezomib
Article Data:	22

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
Appearance:	yellow solid
Risk Codes:	23/24/25-48/23/24/25
Safety:	9-27-36/37-45-60
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

Raw Materials

98-97-5

Downstream Products

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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.