Danegaptide

Base Information

• Chemical Name: Danegaptide
• CAS No.: 943134-39-2
• Molecular Formula: C14H17N3O4
• Molecular Weight: 291.307
• UNII: PA0Y7735AT
• ChEMBL ID: CHEMBL560592
• DSSTox Substance ID: DTXSID201026039
• Metabolomics Workbench ID: 152916
• NCI Thesaurus Code: C83647
• Wikidata: Q27286426
• Mol file: 943134-39-2.mol

Synonyms:danegaptide;ZP1609

Chemical Property of Danegaptide

Chemical Property:

• Boiling Point: 642.4±55.0 °C(Predicted)
• PKA: 2.93±0.40(Predicted)
• PSA: 116.22000
• Density: 1.38±0.1 g/cm3(Predicted)
• LogP: 0.64220
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 291.12190603
• Heavy Atom Count: 21
• Complexity: 420

Purity/Quality:

95-99% ^*data from raw suppliers

GAP-134 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CN(C1C(=O)O)C(=O)CN)NC(=O)C2=CC=CC=C2
• Isomeric SMILES: C1[C@H](CN([C@@H]1C(=O)O)C(=O)CN)NC(=O)C2=CC=CC=C2
• Recent ClinicalTrials: Single Ascending Dose of GAP-134 as a 24-hour IV Infusion in Healthy Japanese Males
• Recent EU Clinical Trials: A Randomised, Double-Blind, Placebo-Controlled, Parallel-Group Trial to Assess Clinical Efficacy and Safety of Danegaptide in Patients with ST-Elevation Myocardial Infarction undergoing Primary Percutaneous Coronary Intervention

Technology Process of Danegaptide

There total 2 articles about Danegaptide 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:

(2S,4R)-4-benzamido-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid (943134-34-7) → (2S,4R)-1-(2-aminoacetyl)-4-benzoylamino-pyrrolidine-2-carboxylic acid (943134-39-2)

Guidance literature:

(2S,4R)-4-benzamido-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 20 ℃; Inert atmosphere; Cooling with ice;

With ammonia; In acetonitrile; at 0 - 20 ℃; for 2.5h;

DOI:10.1016/j.bmcl.2009.07.014

Reference yield:

BOC-glycine (4530-20-5) + benzoic acid (65-85-0,8013-63-6) + (2S,4R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (176486-63-8) → (2S,4R)-1-(2-aminoacetyl)-4-benzoylamino-pyrrolidine-2-carboxylic acid (943134-39-2)

Guidance literature:

Reference yield: 31.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (2S,4R)-1-(2-aminoacetyl)-4-benzoylamino-pyrrolidine-2-carboxylic acid (943134-39-2) → (2S,4R) 4-benzamido-1-(2-(dimethylamino)acetyl)pyrrolidine-2-carboxylic acid

Guidance literature:

formaldehyd; (2S,4R)-1-(2-aminoacetyl)-4-benzoylamino-pyrrolidine-2-carboxylic acid; In methanol; at 0 - 20 ℃; for 3h;

With sodium cyanoborohydride; In methanol; at 20 ℃; for 1.08333h;

upstream raw materials:

BOC-glycine

benzoic acid

(2S,4R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

(2S,4R)-4-benzamido-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid

Refernces

• 1、 -. "Modified lysine-mimetic compounds". Page/Page column 33-34. . Retrieved 2008/06/13.