Ditekiren

Base Information

• Chemical Name: Ditekiren
• CAS No.: 103336-05-6
• Molecular Formula: C50H75 N9 O8
• Molecular Weight: 930.201
• UNII: 5355S3W1IS
• DSSTox Substance ID: DTXSID40145787
• Wikidata: Q27261065
• NCI Thesaurus Code: C95291
• Pharos Ligand ID: TUYCVJ44QNCN
• ChEMBL ID: CHEMBL1790497
• Mol file: 103336-05-6.mol

Synonyms:Boc-Pro-Phe-N-MeHis-Leu(psi)(CHOHCH2)Val-Ile-2-aminomethylpyridine;ditekiren;U 71038;U-71038

Chemical Property of Ditekiren

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1156.6°Cat760mmHg
• Flash Point: 653.3°C
• PSA: 228.05000
• Density: 1.177g/cm³
• LogP: 6.20410
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 25
• Exact Mass: 929.57386038
• Heavy Atom Count: 67
• Complexity: 1600

Purity/Quality:

99% ^*data from raw suppliers

Ditekiren ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)NCC1=CC=CC=N1)NC(=O)C(CC(C(CC(C)C)NC(=O)C(CC2=CN=CN2)N(C)C(=O)C(CC3=CC=CC=C3)NC(=O)C4CCCN4C(=O)OC(C)(C)C)O)C(C)C
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)NCC1=CC=CC=N1)NC(=O)[C@@H](C[C@@H]([C@H](CC(C)C)NC(=O)[C@H](CC2=CN=CN2)N(C)C(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@@H]4CCCN4C(=O)OC(C)(C)C)O)C(C)C
• Uses: Ditekiren, is a potent and specific Renin inhibitor pseudohexapeptide with high metabolic stability.

Technology Process of Ditekiren

There total 14 articles about Ditekiren 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: 85.0%

N-α-<(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl>-Nα-methyl-Nim-tosyl-L-histydyl>-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-methyloctanoyl>-L-isoleucyl>-2-pyridylmethylamine (103336-04-5) → N-α-<(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl>-Nα-methyl-L-histydyl>-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-methyloctanoyl>-L-isoleucyl>-2-pyridylmethylamine (103336-05-6)

Guidance literature:

With benzotriazol-1-ol; In methanol; for 24h; Ambient temperature;

DOI:10.1021/jm00160a049

Reference yield:

2-(Aminomethyl)pyridine (3731-51-9) → N-α-<(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl>-Nα-methyl-L-histydyl>-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-methyloctanoyl>-L-isoleucyl>-2-pyridylmethylamine (103336-05-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 88 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

2: 100 percent / CF₃COOH / CH₂Cl₂ / Ambient temperature

3: 100 percent / Et₃N, diethoxyphosphoryl cyanide / CH₂Cl₂ / Ambient temperature

4: HCl (gas) / diethyl ether / 0.33 h / Ambient temperature

5: Et₃N, diethylphosphoryl cyanide / CH₂Cl₂ / Ambient temperature

6: 5.81 g / CF₃COOH / CH₂Cl₂ / Ambient temperature

7: 78 percent / Et₃N, diethylphosphoryl cyanide / CH₂Cl₂ / Ambient temperature

8: 5.4 g / CF₃COOH / CH₂Cl₂ / Ambient temperature

9: 97 percent / Et₃N, diethoxyphosphoryl cyanide / CH₂Cl₂ / Ambient temperature

10: 85 percent / 1-hydroxybenzotriazole / methanol / 24 h / Ambient temperature

With hydrogenchloride; diethylphosphoryl cyanide; diethyl cyanophosphonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jm00160a049

Reference yield:

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) → N-α-<(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl>-Nα-methyl-L-histydyl>-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-methyloctanoyl>-L-isoleucyl>-2-pyridylmethylamine (103336-05-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 88 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

2: 100 percent / CF₃COOH / CH₂Cl₂ / Ambient temperature

3: 100 percent / Et₃N, diethoxyphosphoryl cyanide / CH₂Cl₂ / Ambient temperature

4: HCl (gas) / diethyl ether / 0.33 h / Ambient temperature

5: Et₃N, diethylphosphoryl cyanide / CH₂Cl₂ / Ambient temperature

6: 5.81 g / CF₃COOH / CH₂Cl₂ / Ambient temperature

7: 78 percent / Et₃N, diethylphosphoryl cyanide / CH₂Cl₂ / Ambient temperature

8: 5.4 g / CF₃COOH / CH₂Cl₂ / Ambient temperature

9: 97 percent / Et₃N, diethoxyphosphoryl cyanide / CH₂Cl₂ / Ambient temperature

10: 85 percent / 1-hydroxybenzotriazole / methanol / 24 h / Ambient temperature

With hydrogenchloride; diethylphosphoryl cyanide; diethyl cyanophosphonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jm00160a049

upstream raw materials:

N-α-<(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl>-N^α-methyl-N^im-tosyl-L-histydyl>-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-methyloctanoyl>-L-isoleucyl>-2-pyridylmethylamine

C₅₀H₇₃N₉O₈

2-(Aminomethyl)pyridine

N-(tert-butyloxycarbonyl)-L-isoleucine

Downstream raw materials:

N-α-acetyl>-L-prolyl>-L-phenylalanyl>-N^α-methyl-L-histydyl>-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-methyloctanoyl>-L-isoleucyl>-(1-oxo-2-pyridyl)methylamine

N-α-acetyl>l-prolyl>-L-phenylalanyl>-N^α-methyl-L-histydyl>-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-methyloctanoyl>-L-isoleucyl>-2-pyridylmethylamine

C₄₉H₇₄N₉O₁₂P

N-α--L-prolyl>-L-phenylalanyl>-N^α-methyl-L-histydyl>-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-methyloctanoyl>-L-isoleucyl>-(1-oxo-2-pyridyl)methylamine

Refernces

• 1、 Thaisrivongs, Suvit,Pals, Donald T.,Harris, Douglas W.,Kati, Warren M.,Turner, Steve R.. "Design and Synthesis of a Potent and Specific Renin Inhibitor with a Prolonged Duration of Action in Vivo". . p. 2088 - 2093. Retrieved 2007/10/02.