Lotrafiban

Base Information

• Chemical Name: Lotrafiban
• CAS No.: 171049-14-2
• Molecular Formula: C₂₃H₃₂N₄O₄
• Molecular Weight: 428.531
• UNII: KLQ306I83X
• DSSTox Substance ID: DTXSID7057602
• Nikkaji Number: J835.875C
• Wikidata: Q27282322
• NCI Thesaurus Code: C81574
• ChEMBL ID: CHEMBL356301
• Mol file: 171049-14-2.mol

Synonyms:(S)-2,3,4,5-tetrahydro-4-methyl-3-oxo-7-((4-(4-piperidyl)piperidino)carbonyl)-1H-1,4-benzodiazepine-2-acetic acid, monohydrochloride;lotrafiban;lotrafiban hydrochloride;SB 214857;SB-214857;SB214857

Chemical Property of Lotrafiban

Chemical Property:

• Boiling Point: 730oC at 760 mmHg
• Flash Point: 395.3oC
• PSA: 101.98000
• Density: 1.22g/cm3
• LogP: 2.10820
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 428.24235551
• Heavy Atom Count: 31
• Complexity: 673

Purity/Quality:

97% ^*data from raw suppliers

1H-1,4-BENZODIAZEPINE-2-ACETIC ACID, 7-([4,4'-BIPIPERIDIN]-1-YLCARBONYL)-2,3,4,5-TETRAHYDRO-4-METHYL-3-OXO-, (2S)- 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC2=C(C=CC(=C2)C(=O)N3CCC(CC3)C4CCNCC4)NC(C1=O)CC(=O)O
• Isomeric SMILES: CN1CC2=C(C=CC(=C2)C(=O)N3CCC(CC3)C4CCNCC4)N[C@H](C1=O)CC(=O)O

Technology Process of Lotrafiban

There total 41 articles about Lotrafiban 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: 90.0%

(2S)-2,3,4,5-tetrahydro-4-methyl-3-oxo-7-[[4-(4-pyridinyl)-1-piperidinyl]carbonyl]-1H-1,4-benzodiazepine-2-acetic acid (363138-98-1) → lotrafiban (171049-14-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In water; isopropyl alcohol; at 75 ℃; for 7.5h; under 3102.97 Torr; Industrial scale;

DOI:10.1021/op034023k

Reference yield: 85.0%

C33H42N4O6 → 7-(4,4'-bipiperidinylcarbonyl)-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid (171049-14-2)

Guidance literature:

With palladium on activated charcoal; ammonium formate; In methanol; Reflux;

DOI:10.1021/op980068n

Reference yield:

C24H34N4O4 + benzyl chloroformate (501-53-1,94274-21-2) → C32H40N4O6 + lotrafiban (171049-14-2)

Guidance literature:

C₂₄H₃₄N₄O₄; With Candida antarctica B (CAB) lipase; In water; at 29 - 30 ℃; for 2.5h; pH=6 - 6.8;

benzyl chloroformate; In dichloromethane; water; at 24 ℃; for 0.5h; pH=6.8 - 7.2;

DOI:10.1021/op025508w

upstream raw materials:

(S)-(-)-7-[1-[1'-(t-butoxycarbonyl)-4,4'-bipiperidinyl]-carbonyl]-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid

(S)-1'-(3-methoxycarbonylmethyl-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepone-7-carbonyl)-[4,4']bipiperidinyl-1-carboxylic acid tert-butyl ester

4-iodo-3-methylbenzoic acid

1-tert-butoxycarbonyl-4,4'-bipiperidine

Refernces

• 1、 Atkins, Richard J.,Banks, Adam,Bellingham, Richard K.,Breen, Gary F.,Carey, John S.,Etridge, Stephen K.,Hayes, Jerome F.,Hussain, Nigel,Morgan, David O.,Oxley, Paul,Passey, Stephen C.,Walsgrove, Timothy C.,Wells, Andrew S.. "The development of a manufacturing route for the GPIIb/IIIa receptor antagonist SB-214857-A. Part 2: Conversion of the key intermediate SB-235349 to SB-214857-A". . p. 663 - 675. Retrieved 2003.
• 2、 Etridge, Stephen K.,Hayes, Jerome F.,Walsgrove, Timothy C.,Wells, Andrew S.. "A new and convergent synthesis of (2S)-7-(4,4′-bipiperidinylcarbonyl)-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H- 1,4-benzodiazepine-2-acetic acid using a palladium-catalysed aminocarbonylation reaction". . p. 60 - 63. Retrieved 1999.