BORTEZOMIB-PINANEDIOL

Base Information

• Chemical Name: BORTEZOMIB-PINANEDIOL
• CAS No.: 205393-22-2
• Molecular Formula: C29H39BN4O4
• Molecular Weight: 518.464
• Mol file: 205393-22-2.mol

Synonyms:Pyrazinecarboxamide, N-[2-[[1-(hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl)-3-methylbutyl]amino]-2-oxo-1-(phenylmethyl)ethyl]-,[3aS-[2[S*(R*)],3aa,4b,6b,7aa]]-;Pyrazinecarboxamide,N-[(1S)-2-[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]-2-oxo-1-(phenylmethyl)ethyl]-(9CI);

Chemical Property of BORTEZOMIB-PINANEDIOL

Chemical Property:

• Appearance/Colour: Yellow solid
• Melting Point: 75-83 °C
• Boiling Point: 719.5±60.0 °C(Predicted)
• PKA: 11.97±0.46(Predicted)
• PSA: 102.44000
• Density: 1.19 g/cm³
• LogP: 4.81780
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform, DMSO (Slightly), Ethanol, Ethyl Acetate, Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

(1R)-(1S,2S,3R,5S)-Pinanediol-N-(N-pyrazinylphenylalaninoyl)-1-amino-3-methyl-butane-1-boronate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of Bortezomib (B675700), a dipeptidyl boronate proteasome inhibitor.

Technology Process of BORTEZOMIB-PINANEDIOL

There total 27 articles about BORTEZOMIB-PINANEDIOL which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.1%

(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 (1310383-72-2,179324-87-9) + N-(pyrazine-2-yl-carbonyl)-L-phenylalanine sodium salt (1093959-75-1) → 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)

Guidance literature:

N-(pyrazine-2-yl-carbonyl)-L-phenylalanine sodium salt; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In dichloromethane; at 0 ℃; for 0.5h;

(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; In dichloromethane; at 0 - 25 ℃; for 24h;

Reference yield: 86.0%

(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 (1310383-72-2,179324-87-9) + (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid (114457-94-2,1608986-16-8) → 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)

Guidance literature:

With 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In dichloromethane; acetonitrile; at -15 - 25 ℃; for 1.5h;

Reference yield: 79.0%

(S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid (114457-94-2,1608986-16-8) + (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride (779357-85-6) → 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)

Guidance literature:

(S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid; With benzotriazol-1-ol; In dichloromethane; at -5 ℃; for 0.333333h;

(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -15 - 20 ℃; for 3h;

DOI:10.1021/jm9005093

upstream raw materials:

2-pyrazylcarboxylic acid

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

(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

N-(pyrazine-2-yl-carbonyl)-L-phenylalanine sodium salt

Downstream raw materials:

bortezomib

velcade

Refernces

• 1、 Hinkes, Stefan P.A.,Klein, Christian D.P.. "Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids". supporting information. p. 3048 - 3052. Retrieved 2019/05/10.
• 2、 -. "Proteasome inhibitor delanzomib for use in the treatment of lupus". . . Retrieved 2016/06/06.