Bortezomib intermediates II

Product Name: Bortezomib intermediates II
CAS No.: 205393-21-1
Chemical Name: Bortezomib intermediates II
Synonyms: Atrazine Impurity 11;Bortezomib intermediates I;Bortezomib Impurity 54 HCl;BortezoMib InterMediate II;Bortezomib intermediates II;BortezoMib interMediates N-2;(alphaS)-alpha-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodi;(S)-2-amino-N-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-3-phenylpropanamide hydrochloride;(αS)-α-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]-benzenepropanamide Monohydrochloride;(alphaS)-alpha-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]benzenepropanamide hydrochloride
CBNumber: CB72505953
Molecular Formula: C24H38BClN2O3
Formula Weight: 448.83412
MOL File: 205393-21-1.mol

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Bortezomib intermediates II Property

Melting point:: 197-198℃
storage temp.: Inert atmosphere,Store in freezer, under -20°C

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H290May be corrosive to metals

H314Causes severe skin burns and eye damage

Precautionary statements

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P363Wash contaminated clothing before reuse.

P390Absorb spillage to prevent material damage.

P402Store in a dry place.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

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N-Bromosuccinimide Price

TRC

Product number: A609965
Product name: (αS)-α-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]-benzenepropanamideMonohydrochloride
Packaging: 100mg
Price: $1540
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA151451
Product name: (alphaS)-alpha-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]benzenepropanamideHydrochloride
Packaging: 2mg
Price: $59
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA151451
Product name: (alphaS)-alpha-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]benzenepropanamideHydrochloride
Packaging: 5mg
Price: $117
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA151451
Product name: (alphaS)-alpha-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]benzenepropanamideHydrochloride
Packaging: 10mg
Price: $203
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA151451
Product name: (alphaS)-alpha-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]benzenepropanamideHydrochloride
Packaging: 25mg
Price: $405
Updated: 2021/12/16

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Bortezomib intermediates II Chemical Properties,Usage,Production

Uses

(αS)-α-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]-benzenepropanamide Monohydrochloride is a Bortezomib (B675700) intermediate which is used in the evaluation of bone-targeted proteasome inhibitors for myeloma.

Synthesis

7647-01-0

1187479-72-6

205393-21-1

GENERAL METHODS: (S)-N-Boc-2-amino-3-methoxypropionic acid (4.73 g, 21.58 mmol) was dissolved in anhydrous CH2Cl2 (120 mL) and cooled to -10 °C. HOBt (4.38 g, 32.37 mmol) and EDCI (6.2 g, 32.37 mmol) were added sequentially and stirred for 10 minutes. Intermediate 5 (8.19 g, 21.58 mmol) and DIPEA (9.77 g, 75.53 mmol) were then added. The reaction mixture was stirred at -10 °C for 1 hour, followed by continued stirring at room temperature for 15 hours. After completion of the reaction, the organic phase was washed sequentially with 10% hydrochloric acid, 5% NaHCO3 solution and brine and dried over anhydrous Na2SO4. Filtered and concentrated, the crude product obtained was directly used in the next step of the reaction. The borate ester prepared above was dissolved in ethyl acetate (30 mL) and ethyl acetate solution (55 mL) of 4.5 mol/L HCl was added slowly and dropwise at 0 °C. The reaction mixture was stirred at room temperature for 2 h. The ethyl acetate was removed by evaporation under reduced pressure. Methyl tert-butyl ether (MTBE) was added to the residue and filtered to give the glassy solid product 3a (7.8 g, 89.7% yield). The product was confirmed by 1H NMR (400 MHz, DMSO) and MS (ESI) characterization.

References

[1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 3975 - 3981
[2] Journal of Medicinal Chemistry, 2018,

Bortezomib intermediates II Preparation Products And Raw materials

Raw materials

Preparation Products

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Bortezomib intermediates II Suppliers

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205393-21-1, Bortezomib intermediates IIRelated Search:

Isovaleraldehyde Bortezomib Impurity 8 4,6-Methano-1,3,2-benzodioxaborole,2-[(1S)-1-chloro-3-Methylbutyl]hexahydro-3a,5,5-triMethyl-,(3aS,4S,6S,7aR)- Bortezomib Impurity 57 (1S,2S,3R,5S)-PinanediolN-BOC-L-phenylalanine-L-leucine boronate (R)-3-phenyl-2-(pyrazine-2-carboxaMido)propanoic acid BORTEZOMIB-PINANEDIOL 3,6-Dibenzylhexahydropyrazine-2,5-dione Bortezomib Impurity 52 Bortezomib Impurity 9 Desisobutyl-n-butyl BortezoMib (IS,2S,3R,5S)-Pinanediol-L-phenylalanine-L-leucine boronate, HCl salt (S,E)-N-(1-((3-methylbut-1-en-1-yl)amino)-1-oxo-3-phenylpropan-2-yl) pyrazine-2-carboxamide Bortezomib Impurity 32 (S)-(+)-PINANEDIOL (DICHLORMETHYL)BORONATE Bortezomib Impurity 47 HCl Bortezomib Impurity 60 4,6-Methano-1,3,2-benzodioxaborole-2-methanamine

Bortezomib Impurity 54 HCl

(S)-2-amino-N-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-3-phenylpropanamide hydrochloride

Bortezomib intermediates II

(alphaS)-alpha-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]benzenepropanamide hydrochloride

BortezoMib InterMediate II

BortezoMib interMediates N-2

(αS)-α-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]-benzenepropanamide Monohydrochloride

Bortezomib intermediates I

BenzenepropanaMide, a-aMino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-triMethyl-4,6-Methano-1,3,2-benzodioxaborol-2-yl]-3-Methylbutyl]-, hydrochloride (1:1), (aS)

(αS)-α-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]benzenepropanamide Hydrochloride (Bortezomib Intermediate II)

(alphaS)-alpha-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]benzenepropanamide Hydrochloride (Bortezomib Intermediate II)

Atrazine Impurity 11

(alphaS)-alpha-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodi

(αS)-α-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]-benzenepropanamide monohydrochloride, CAS 205393-21-1

(alphaS)-alpha-Amino-N-[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]-benzenepropanamide Monohydrochloride

205393-21-1

C24H37BN2O3HCl

C24H38BClN2O3

C24H37BN2O3ClH