3(S)-[1-[3-(4-Piperidinyl)propionyl]piperidin-3(R)-ylcarboxamido]-3-(3-pyridyl)propionic acid

Base Information

• Chemical Name: 3(S)-[1-[3-(4-Piperidinyl)propionyl]piperidin-3(R)-ylcarboxamido]-3-(3-pyridyl)propionic acid
• CAS No.: 198958-88-2
• Molecular Formula: C22H32N4O4
• Molecular Weight: 416.5139
• Mol file: 198958-88-2.mol

Synonyms:Elarofiban [INN];(S)-beta-((R)-1-(3-(4-Piperidyl)propionyl)nipecotamido)-3-pyridinepropionic acid;Elarofiban;(3S)-3-[[(3R)-1-[3-(4-piperidyl)propanoyl]piperidine-3-carbonyl]amino]-3-pyridin-3-yl-propanoic acid;

Chemical Property of 3(S)-[1-[3-(4-Piperidinyl)propionyl]piperidin-3(R)-ylcarboxamido]-3-(3-pyridyl)propionic acid

Chemical Property:

• Vapor Pressure: 1E-21mmHg at 25°C
• Refractive Index: 1.554
• Boiling Point: 719.5 °C at 760 mmHg
• Flash Point: 388.9 °C
• Density: 1.203g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3(S)-[1-[3-(4-Piperidinyl)propionyl]piperidin-3(R)-ylcarboxamido]-3-(3-pyridyl)propionic acid

There total 18 articles about 3(S)-[1-[3-(4-Piperidinyl)propionyl]piperidin-3(R)-ylcarboxamido]-3-(3-pyridyl)propionic acid 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:

C30H38N4O6 → [S-(R*,S*)]-β-[[[1-[1-oxo-3-(4-piperidinyl)propyl]-3-piperidinyl]carbonyl]amino]-3-pyridine propanoic acid (198958-88-2)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 38 - 42 ℃; for 2h; under 1500.15 - 2250.23 Torr; Large scale;

DOI:10.1021/op034103o

Reference yield:

3-(4-pyridinyl)-2-propenoic acid (5337-79-1) → [S-(R*,S*)]-β-[[[1-[1-oxo-3-(4-piperidinyl)propyl]-3-piperidinyl]carbonyl]amino]-3-pyridine propanoic acid (198958-88-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Rh/Al₂O₃; hydrogen; ammonium hydroxide / water / 8 h / 85 - 95 °C / 2250.23 - 2625.26 Torr / pH 7.5 / Large scale

2.1: calcium hydroxide / water; acetonitrile / 2.5 h / 0 - 10 °C / Inert atmosphere

3.1: calcium hydroxide; benzotriazol-1-ol / water; tetrahydrofuran / pH 7 / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

4.1: lithium hydroxide; water / tetrahydrofuran / 0 - 5 °C / Inert atmosphere

5.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / acetonitrile / Inert atmosphere

6.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Large scale

7.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 38 - 42 °C / 1500.15 - 2250.23 Torr / Large scale

With ammonium hydroxide; lithium hydroxide monohydrate; palladium on activated charcoal; Rh/Al₂O₃; water; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; calcium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1021/op034103o

Reference yield:

N-Boc-3-(4-piperidinepropionyl)-(R)-(-)-nipecotyl-[(S)-3-amino-3-(3-pyridyl)]propionic acid (223697-42-5) → [S-(R*,S*)]-β-[[[1-[1-oxo-3-(4-piperidinyl)propyl]-3-piperidinyl]carbonyl]amino]-3-pyridine propanoic acid (198958-88-2)

Guidance literature:

With hydrogenchloride; methoxybenzene; In 1,4-dioxane; for 3h;

DOI:10.1021/jm990418b

upstream raw materials:

N-Boc-3-(4-piperidinepropionyl)-(R)-(-)-nipecotyl-[(S)-3-amino-3-(3-pyridyl)]propionic acid

methyl (S)-3-amino-3-pyridin-3-ylpropionate

(S)-3-[((R)-Piperidine-3-carbonyl)-amino]-3-pyridin-3-yl-propionic acid methyl ester

4-{3-[(R)-3-((S)-2-Methoxycarbonyl-1-pyridin-3-yl-ethylcarbamoyl)-piperidin-1-yl]-3-oxo-propyl}-piperidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Hoekstra, William J.,Maryanoff, Bruce E.,Damiano, Bruce P.,Andrade-Gordon, Patricia,Cohen, Judith H.,Costanzo, Michael J.,Haertlein, Barbara J.,Hecker, Leonard R.,Hulshizer, Becky L.,Kauffman, Jack A.,Keane, Patricia,McComsey, David F.,Mitchell, John A.,Scott, Lorraine,Shah, Rekha D.,Yabut, Stephen C.. "Potent, orally active GPIIb/IIIa antagonists containing a nipecotic acid subunit. Structure-activity studies leading to the discovery of RWJ-53308". . p. 5254 - 5265. Retrieved 2007/10/03.