Unii-kxl5BC5A6F

Base Information

• Chemical Name: Unii-kxl5BC5A6F
• CAS No.: 171964-73-1
• Molecular Formula: C₂₄H₃₂F₃N₃O₅
• Molecular Weight: 499.53
• UNII: KXL5BC5A6F
• DSSTox Substance ID: DTXSID80938074
• Nikkaji Number: J882.106B
• Wikidata: Q82914324
• Pharos Ligand ID: S3SB6PVKM9NR
• ChEMBL ID: CHEMBL55210
• Mol file: 171964-73-1.mol

Synonyms:ZD 0892;ZD-0892

Chemical Property of Unii-kxl5BC5A6F

Chemical Property:

• PSA: 104.81000
• LogP: 3.43250
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 499.22940562
• Heavy Atom Count: 35
• Complexity: 779

Purity/Quality:

99%min ^*data from raw suppliers

ZD-0892 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C(C(=O)C(F)(F)F)NC(=O)C1CCCN1C(=O)C(C(C)C)NC(=O)C2=CC=C(C=C2)OC
• Isomeric SMILES: CC(C)[C@@H](C(=O)C(F)(F)F)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)C)NC(=O)C2=CC=C(C=C2)OC

Technology Process of Unii-kxl5BC5A6F

There total 13 articles about Unii-kxl5BC5A6F 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: 87.0%

(S)-1-[(S)-2-(4-methoxybenzamido)-3-methylbutyryl]-N-[2-methyl-1-(2,2,2-trifluoro-1-hydroxyethyl)propyl]pyrrolidine-2-carboxamide → (S)-1-[(S)-2-(4-Methoxy-benzoylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid (3,3,3-trifluoro-1-isopropyl-2-oxo-propyl)-amide (171964-73-1)

Guidance literature:

With dichloro-acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In toluene; for 18h; Ambient temperature;

DOI:10.1021/jm960819g

Reference yield: 65.0%

(S)-1-[(S)-2-(4-methoxybenzamido)-3-methylbutyryl]-N-[(S)-2-methyl-1-((R)-2,2,2-trifluoro-1-hydroxyethyl)propyl]pyrrolidine-2-carboxamide (171964-75-3) → (S)-1-[(S)-2-(4-methoxybenzamido)-3-methylbutyryl]-N-[(S)-2-methyl-1-(trifluoroacetyl)propyl]pyrrolidine-2-carboxamide (171964-73-1)

Guidance literature:

With sodium hydroxide; potassium permanganate; In water; tert-butyl alcohol; at 0 ℃; for 1h;

DOI:10.1021/jm970250z

Reference yield:

4-methoxy-benzoyl chloride (100-07-2) → (S)-1-[(S)-2-(4-methoxybenzamido)-3-methylbutyryl]-N-[(S)-2-methyl-1-(trifluoroacetyl)propyl]pyrrolidine-2-carboxamide (171964-73-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / Et₃N / tetrahydrofuran / 1 h

2: 6.5 g / TFA / 0.5 h

3: 65 percent / N-hydroxybenzotriazole hydrate, Et₃N, EDC / dimethylformamide / 12 h

4: 65 percent / NaOH, KMnO₄ / 2-methyl-propan-2-ol; H₂O / 1 h / 0 °C

With sodium hydroxide; potassium permanganate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm970250z

upstream raw materials:

4-methoxy-benzoyl chloride

(S)-1-[(S)-2-(4-methoxybenzamido)-3-methylbutyryl]-N-[(S)-2-methyl-1-((R)-2,2,2-trifluoro-1-hydroxyethyl)propyl]pyrrolidine-2-carboxamide

L-valyl-L-proline tert-butyl ester

(4-methoxybenzoyl)-L-valyl-L-proline

Refernces

• 1、 Veale, Chris A.,Bernstein, Peter R.,Bohnert, Claudia M.,Brown, Frederick J.,Bryant, Craig,Damewood Jr., James R.,Earley, Roger,Feeney, Scott W.,Edwards, Philip D.,Gomes, Bruce,Hulsizer, James M.,Kosmider, Ben J.,Krell, Robert D.,Moore, Gary,Salcedo, Theodora W.,Shaw, Andrew,Silberstein, David S.,Steelman, Gary B.,Stein, Mark,Strimpler, Anne,Thomas, Roy M.,Vacek, Edward P.,Williams, Joseph C.,Wolanin, Donald J.,Woolson, Sheila. "Orally active trifluoromethyl ketone inhibitors of human leukocyte elastase". . p. 3173 - 3181. Retrieved 2007/10/03.