Sampatrilat

Base Information

• Chemical Name: Sampatrilat
• CAS No.: 129981-36-8
• Molecular Formula: C26H40 N4 O9 S
• Molecular Weight: 584.691
• UNII: V7O29949TG
• DSSTox Substance ID: DTXSID6057877
• Nikkaji Number: J776.754D
• Wikidata: Q27291638
• NCI Thesaurus Code: C132269
• Pharos Ligand ID: QRDCSQ4P51DU
• ChEMBL ID: CHEMBL42583
• Mol file: 129981-36-8.mol

Synonyms:N-(1-(2-carboxy-3-(N(2)-mesyllysylamino)propyl)-1-cyclopentylcarbonyl)tyrosine;sampatrilat;UK 81,252;UK 81252;UK-81,252;UK-81252

Chemical Property of Sampatrilat

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 240.58000
• Density: 1.343g/cm³
• LogP: 4.31350
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 17
• Exact Mass: 584.25160004
• Heavy Atom Count: 40
• Complexity: 971

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)NC(CCCCN)C(=O)NCC(CC1(CCCC1)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)O)C(=O)O
• Isomeric SMILES: CS(=O)(=O)N[C@@H](CCCCN)C(=O)NC[C@H](CC1(CCCC1)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)O)C(=O)O

Technology Process of Sampatrilat

There total 7 articles about Sampatrilat 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:

(S,S,S)-N-{1-[3-(N6-benzyloxycarbonyl-N2-mesyllysylamino)-2-carboxypropyl]-1-cyclopentylcarbonyl}tyrosine → (S,S,S)-N-{1-[2-carboxy-3-(N-mesyllysylamino)propyl]-1-cyclopentylcarbonyl}tyrosine (129981-36-8)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; sodium hydroxide; In ethyl acetate; at 21 - 29 ℃; for 7h; under 3102.97 Torr; Large scale;

DOI:10.1021/op020091f

Reference yield:

(S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid (129982-29-2) → (S,S,S)-N-{1-[2-carboxy-3-(N-mesyllysylamino)propyl]-1-cyclopentylcarbonyl}tyrosine (129981-36-8)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydroxide / water; dichloromethane / pH 8.5 - 9 / Large scale

2: 5%-palladium/activated carbon; hydrogen / ethanol / 25 - 35 °C / 2585.81 - 3102.97 Torr / Large scale

3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 10 - 20 °C / Large scale

4: trifluoroacetic acid; methoxybenzene / dichloromethane / 6 h / 30 - 35 °C / Large scale

5: sodium hydroxide; 5%-palladium/activated carbon; hydrogen / ethyl acetate / 7 h / 21 - 29 °C / 3102.97 Torr / Large scale

With 5%-palladium/activated carbon; hydrogen; benzotriazol-1-ol; methoxybenzene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; sodium hydroxide; In ethanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/op020091f

Reference yield:

tert-butyl (S)-N-(1-{2-tert-butoxycarbonyl-3-benzylaminopropyl}-1-cyclopentylcarbonyl)-O4-tert-butyltyrosinate → (S,S,S)-N-{1-[2-carboxy-3-(N-mesyllysylamino)propyl]-1-cyclopentylcarbonyl}tyrosine (129981-36-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 30 - 40 °C / 2844.39 - 3102.97 Torr / Large scale

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 10 - 20 °C / Large scale

3: trifluoroacetic acid; methoxybenzene / dichloromethane / 6 h / 30 - 35 °C / Large scale

4: sodium hydroxide; 5%-palladium/activated carbon; hydrogen / ethyl acetate / 7 h / 21 - 29 °C / 3102.97 Torr / Large scale

With 5%-palladium/activated carbon; hydrogen; benzotriazol-1-ol; methoxybenzene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; sodium hydroxide; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1021/op020091f

upstream raw materials:

tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O₄-tert-butyltyrosinate

(S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid