Denagliptin tosylate

Base Information

• Chemical Name: Denagliptin tosylate
• CAS No.: 811432-66-3
• Molecular Formula: C20H18F3N3O.C7H8O3S
• Molecular Weight: 545.57300
• UNII: T47477CUF7
• ChEMBL ID: CHEMBL2104962
• DSSTox Substance ID: DTXSID90230915
• NCI Thesaurus Code: C72735
• Mol file: 811432-66-3.mol

Synonyms:Denagliptin tosylate;811432-66-3;Denagliptin tosylate [USAN];GW823093C;Denagliptin tosilate;UNII-T47477CUF7;T47477CUF7;GW 823093C;GW-823093C;Denagliptin tosylate (USAN);2-Pyrrolidinecarbonitrile, 1-((2S)-2-amino-3,3-bis(4-fluorophenyl)-1-oxopropyl)-4-fluoro-, (2S,4S)-, mono(4-methylbenzenesulfonate);(2S,4S)-1-((2S)-2-Amino-3,3-bis(4-fluorophenyl)propanoyl)-4-fluoropyrrolidine-2-carbonitrile 4-methylbenzenesulfonate;(2S,4S)-1-[(2S)-2-amino-3,3-bis(4-fluorophenyl)propanoyl]-4-fluoropyrrolidine-2-carbonitrile;4-methylbenzenesulfonic acid;redona;(2S,4S)-1-[(2S)-2-Amino-3,3-bis(4-fluorophenyl)propanoyl]-4-fluoropyrrolidine-2-carbonitrile 4-methylbenzenesulfonate;SCHEMBL4801510;CHEMBL2104962;DTXSID90230915;MSCWUTTUQLYJFT-QMBKNIKNSA-N;811432-66-3 (tosylate);AKOS040751527;(2S,4S)-1-((S)-2-amino-3,3-bis(4-fluorophenyl)propanoyl)-4-fluoropyrrolidine-2-carbonitrile 4-methylbenzenesulfonate;D06578;Q27289648;(2S,4S)-4-fluoro-1-[4-fluoro-beta-(4-fluorophenyl)-L-phenylalanyl]-2-pyrrolidinecarbonitrile p-toluenesulfonic acid salt

Chemical Property of Denagliptin tosylate

Chemical Property:

• Melting Point: 241-245 °C (decomp)(Solv: isopropanol (67-63-0); water (7732-18-5))
• PSA: 132.87000
• LogP: 5.84728
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 545.15961198
• Heavy Atom Count: 38
• Complexity: 748

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.C1C(CN(C1C#N)C(=O)C(C(C2=CC=C(C=C2)F)C3=CC=C(C=C3)F)N)F
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.C1[C@@H](CN([C@@H]1C#N)C(=O)[C@H](C(C2=CC=C(C=C2)F)C3=CC=C(C=C3)F)N)F

Technology Process of Denagliptin tosylate

There total 2 articles about Denagliptin tosylate 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: 88.0%

(S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid (481055-29-2) + (2S,4S)-4-fluoropyrrolidine-2-carbonitrile; 4-methylbenzene-1-sulfonic acid (483366-11-6) + toluene-4-sulfonic acid (104-15-4) → denagliptin tosylate (811432-66-3)

Guidance literature:

(S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid; (2S,4S)-4-fluoropyrrolidine-2-carbonitrile; 4-methylbenzene-1-sulfonic acid; With N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 0 ℃; for 0.5h; Large scale reaction;

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; at 0 - 20 ℃; Large scale reaction;

toluene-4-sulfonic acid; With isopropyl alcohol; at 60 ℃; for 6h; Large scale reaction;

DOI:10.1021/op900178d

Reference yield: 70.0%

tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate (483368-24-7) + toluene-4-sulfonic acid (104-15-4) → denagliptin tosylate (811432-66-3)

Guidance literature:

In ethanol; at 60 ℃; for 12h;

upstream raw materials:

tert-butyl {(1S)-1-[bis(4-fluorophenyl)methyl]-2-[(2S)-cyano-(4S)-fluoro-1-pyrrolidinyl]-2-oxoethyl}carbamate

toluene-4-sulfonic acid

(S)-2-((tert-butoxycarbonyl)amino)-3,3-bis(4-fluorophenyl)propanoic acid

(2S,4S)-4-fluoropyrrolidine-2-carbonitrile; 4-methylbenzene-1-sulfonic acid