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179324-69-7 Usage

Chemical Properties

Yellow Solid

Originator

Millenium (LeukoSite, Proscript) (US)

General Description

Proteasomes normally function to degrade proteins that areno longer needed by the cell. Such proteins are normallymarked by the addition of ubiquitin, a 76 amino acid proteinthat is added to the -amino group of lysine residues onthe target proteins. The marked proteins are then hydrolyzedby the large barrel-shaped proteasomes to givepeptides of 7 to 8 residues that may be further hydrolyzedand reutilized by the cell. This process serves to regulateprotein levels within the cell, remove defective proteins,and becomes important in maintaining normal signal transduction.Inhibition of the proteasomes results in the buildup of ubiquitylated proteins, which disrupts cell-signalingprocesses and cell growth. The signaling bytranscription factor NF-B (nuclear factor B) appears tobe especially sensitive to bortezomib. NF-B is associatedwith the transcription of antiapoptotic and proliferativegenes but is under the control of IB (inhibitor of NF-B).IB can itself be phosphorylated by IKK (IB kinase),which marks IB for ubiquitylation and destruction allowingNF-B to mediate its antiapoptotic and proliferative effects effects.In the presence of the competitive inhibitor bortezomib(IC50=0.6 nM), the 26S proteasome is inhibitedand the ubiquitylated IkB is still capable of inhibiting NF-kB, preventing its effects.

Chemical Synthesis

Although the synthesis of dipeptidyl boronic acids have appeared on several reports, the synthetic details for bortezomib were not revealed. The synthetic route for the preparation of bortezomib is depicted in the scheme.The pinanediol ester of leucine boronic acid (56)was coupled with N-Boc phenylalanine (57) in the presence of TBTU followed by deprotection of the Boc group to provide 58. N-Acylation of 58 then furnished the dipeptide boronate ester 60. Deprotection of the boronic ester functionality was achieved by bi-phase transfer esterification with isobutyl boronic acid. Bortezomib (VI) was isolated by extractive workup.

Definition

ChEBI: L-Phenylalaninamide substituted at the amide nitrogen by a 1-(dihydroxyboranyl)-3-methylbutyl group and at Nalpha by a pyrazin-2-ylcarbonyl group. It is a dipeptidyl boronic acid tha reversibly inhibits the 26S proteasome.

Uses

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 cells. T

Drug for Cancer treatment

Bortezomib is a drug for treatment of hematopoietic malignancies with the appearance being white or white-like crystalline powder. It is easily soluble in dimethyl sulfoxide, ethanol, but insoluble in aqueous solution. This product is the reversible inhibitor of the mammal cell 26S proteasome chymotrypsin-like activity. 26S proteasome is a large protein complex which can degrade ubiquitin. Ubiquitin proteasome pathway plays an important role in regulation of the intracellular concentration of specific proteins in order to maintain the stability of the intracellular environment. Proteolytic affects intracellular multi-level signalling cascade. The disruption of the normal intracellular environment can lead to cell death while the inhibition of the 26S proteasome can prevent the hydrolysis of specific proteins. In vitro tests have proved bortezomib exhibits cytotoxicity to multiple types of cancer cells. The in vivo models of preclinical tumor have proved that bortezomib is capable of delaying the tumor growth of multiple myeloma which is suitable for the treatment of multiple myeloma. The above information is edited by the Chemicalbook of Dai Xiongfeng.

Description

Bortezomib, a potent ubiquitin proteasome (26S) inhibitor (Ki=0.6 nM), was launched in the US as a treatment for multiple myeloma. This proteasome is required for the proteolytic degradation of the majority of cellular proteins and is present in all cells. It is required for the control of inflammatory processes, cell cycle regulation and gene expression and is a novel target in cancer treatment. Bortezomib is a N-acyl-pseudodipeptidyl boronic acid and formulated as a mannitol ester. Aldehyde containing peptides are also proteasome inhibitors, but lack chiral stability (racemization) and selectivity against other proteases including cysteine proteases. Replacement of the aldehyde moiety by a boronic acid avoids these shortcomings and provides some measure of selective proteasome inhibition relative to many other serine proteases. It is prepared by coupling the pinanediol ester of leucine boronic acid with N-tert-Bocphenylalanine utilizing O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) as the coupling agent. The tert-Boc protecting group is then cleaved from the dipeptide and pyrazinecarboxylic acid is coupled to form the terminal amide. Hydrolysis of the boronate ester is accomplished via a two-phase transesterification procedure using isobutyl boronic acid and aqueous extraction. In a study of patients who had received at least two prior therapies and demonstrated disease progression on their most recent therapy, about twenty eight percent showed a response to bortezomib. The response lasted a median time of one year. Another trial in 54 patients with relapsed multiple myeloma showed similar responses. It is dosed intravenously at an exposure of 1.3 mg/m2/dose twice weekly for two weeks followed by a 10-day drug-holiday. At therapeutic doses, the plasma drug levels were reported to drop to near detection limits within minutes of intravenous dosing. Based upon an ex vivo proteasome activity assay using blood cells, the pharmacodynamic half-life ranged from 9 to 15 h in patients with advanced malignancies.

Brand name

Velcade (Millennium).

Pharmaceutical Applications

Bortezomib belong to the class of drugs called proteasome inhibitors and is licensed in the United States and the United Kingdom for the treatment of multiple myeloma. The drug has been licensed for patients in whom the myeloma has progressed despite prior treatment or where a bone marrow transplant is not possible or was not successful. It is marketed under the name Velcade? or Cytomib?. Velcade is administered via injection and is sold as powder for reconstitution. Bortezomib was the first drug approved in the new drug class of proteasome inhibitors and boron seems to be its active element. For the mode of action, it is believed that the boron atom binds with high affinity and specificity to the catalytic site of 26S proteasome and inhibits its action. Therapy with Bortezomib can lead to a variety of adverse reactions, including peripheral neuropathy, myelosuppression, renal impairment and gastrointestinal (GI) disturbances together with changes in taste. Nevertheless, the side effects are in most cases less severe than with alternative treatment options such as bone marrow transplantation.

Description

Bortezomib, a modified dipeptidyl boronic acid, is a therapeutic proteasome inhibitors used for the treatment of cancers. It is indicated for the treatment of relapsed multiple myeloma and mantle cell lymphoma. It is capable of inhibiting the mammalian 26S proteasome, which is important in regulating the intracellular concentration of specific proteins to maintain homeostasis within cells. The disruption of 26S proteasome function disrupts normal cellular homeostasis, leading to cytotoxic effect on various kinds of cancer cells.
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-/m0/s1

179324-69-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Bortezomib

1.2 Other means of identification

Product number -
Other names VELCADE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:179324-69-7 SDS

179324-69-7Synthetic route

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

bortezomib pinacol ester
1029701-48-1

bortezomib pinacol ester

velcade
179324-69-7

velcade

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

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

velcade
179324-69-7

velcade

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 20℃; for 40h;92%
C24H33BN4O4

C24H33BN4O4

velcade
179324-69-7

velcade

Conditions
ConditionsYield
With hydrogenchloride; 2-methyl-propan-1-ol In methanol; pentane at 0 - 20℃; for 12h; Large scale;86%
C26H37BN4O4

C26H37BN4O4

velcade
179324-69-7

velcade

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

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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20℃;82.3%
C25H35BN4O4

C25H35BN4O4

velcade
179324-69-7

velcade

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

velcade
179324-69-7

velcade

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%
Dihydroxy-isobutyl-boran
84110-40-7

Dihydroxy-isobutyl-boran

C29H39BN4O4

C29H39BN4O4

velcade
179324-69-7

velcade

Conditions
ConditionsYield
With hydrogenchloride In methanol; n-heptane; water at 0 - 25℃; for 2h;71.5%
2-pyrazylcarboxylic acid
98-97-5

2-pyrazylcarboxylic acid

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

N-benzyl-L-phenylalanine

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

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

velcade
179324-69-7

velcade

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%
2-pyrazylcarboxylic acid
98-97-5

2-pyrazylcarboxylic acid

C23H27BNO5Pol

C23H27BNO5Pol

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

velcade
179324-69-7

velcade

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

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

phenylboronic acid
98-80-6

phenylboronic acid

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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%
bortezomib pinacol ester
1029701-48-1

bortezomib pinacol ester

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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
2-pyrazylcarboxylic acid
98-97-5

2-pyrazylcarboxylic acid

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

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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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

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

A

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

[(1S)-1-[[(2S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]-1-oxopropyl]amino]-3-methylbutyl]boronic acid

B

velcade
179324-69-7

velcade

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20℃;
C32H43BN2O5

C32H43BN2O5

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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
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
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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane
2: methanol / Acidic conditions
View Scheme
N-Cbz-L-Phe
1161-13-3

N-Cbz-L-Phe

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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
2-pyrazylcarboxylic acid
98-97-5

2-pyrazylcarboxylic acid

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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

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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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
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
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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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

(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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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

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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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

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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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

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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
With hydrogenchloride; Dihydroxy-isobutyl-boran In hexane; 1,1,1-trideuteromethanol; water at 0 - 20℃; Concentration; Temperature; Large scale;
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

velcade
179324-69-7

velcade

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

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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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

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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
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

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

velcade
179324-69-7

velcade

Conditions
ConditionsYield
With hydrogenchloride; Dihydroxy-isobutyl-boran In methanol; n-heptane; water at 20 - 30℃; for 1.5h;4.2 g
acetone
67-64-1

acetone

phenylboronic acid
98-80-6

phenylboronic acid

velcade
179324-69-7

velcade

Conditions
ConditionsYield
With hydrogenchloride In hexane; acetonitrile
velcade
179324-69-7

velcade

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

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

Conditions
ConditionsYield
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

C16H29N3O4

velcade
179324-69-7

velcade

C35H50BN7O6

C35H50BN7O6

Conditions
ConditionsYield
In chloroform-d1 at 45℃;95%
pinanediol

pinanediol

velcade
179324-69-7

velcade

C29H39BN4O4

C29H39BN4O4

Conditions
ConditionsYield
In toluene for 3h; Inert atmosphere; Reflux;91.2%
dopamine folic acid

dopamine folic acid

velcade
179324-69-7

velcade

C46H49BN12O9

C46H49BN12O9

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃;80%
velcade
179324-69-7

velcade

bortezomib
390800-88-1

bortezomib

Conditions
ConditionsYield
In isopropyl alcohol; acetonitrile at 20℃; for 4h; Product distribution / selectivity;76.9%
citric acid
77-92-9

citric acid

velcade
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

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
ConditionsYield
In ethyl acetate at 20 - 74℃; for 3h;71.1%
C14H29N3O6

C14H29N3O6

velcade
179324-69-7

velcade

C33H50BN7O8

C33H50BN7O8

Conditions
ConditionsYield
In chloroform-d170%
velcade
179324-69-7

velcade

A

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

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

B

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

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

Conditions
ConditionsYield
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;
velcade
179324-69-7

velcade

A

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

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

B

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

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

C

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

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

Conditions
ConditionsYield
With dihydrogen peroxide In water at 20℃; for 1h; Kinetics; Product distribution; Further Variations:; Solvents; Oxidation; hydrolysis;
velcade
179324-69-7

velcade

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

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

Conditions
ConditionsYield
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;
dopamine hydrochloride
62-31-7

dopamine hydrochloride

velcade
179324-69-7

velcade

C27H33BN5O5(1-)*H(1+)

C27H33BN5O5(1-)*H(1+)

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