Cyprodime

Base Information

• Chemical Name: Cyprodime
• CAS No.: 118111-54-9
• Molecular Formula: C₂₂H₂₉NO₃
• Molecular Weight: 355.477
• UNII: 2C6F5L8S8X
• DSSTox Substance ID: DTXSID90922601
• Wikipedia: Cyprodime
• Pharos Ligand ID: PC7RRGV3JRUC
• ChEMBL ID: CHEMBL322796
• Mol file: 118111-54-9.mol

Synonyms:cyprodime;cyprodime hydrobromide;N-(cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one

Chemical Property of Cyprodime

Chemical Property:

• Vapor Pressure: 2.75E-10mmHg at 25°C
• Melting Point: 155-159 °C(Solv: methanol (67-56-1))
• Boiling Point: 504°Cat760mmHg
• PKA: 7.42±0.40(Predicted)
• Flash Point: 258.6°C
• PSA: 38.77000
• Density: 1.21g/cm³
• LogP: 3.04950
• Storage Temp.: Desiccate at +4°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 355.21474379
• Heavy Atom Count: 26
• Complexity: 576

Purity/Quality:

98%Min ^*data from raw suppliers

Cyprodime hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC2=C1C34CCN(C(C2)C3(CCC(=O)C4)OC)CC5CC5
• Isomeric SMILES: COC1=CC=CC2=C1[C@]34CCN([C@H](C2)[C@@]3(CCC(=O)C4)OC)CC5CC5

Technology Process of Cyprodime

There total 10 articles about Cyprodime 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: 67.0%

17-(cyclopropylmethyl)-4-hydroxy-14β-methoxymorphinan-6-one (124919-20-6) + phenyltrimethylammonium chloride (138-24-9) → cyprodime (118111-54-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 6.5h;

Reference yield:

(-)-4,14-dimethoxymorphinan-6-one (118111-53-8) + chloro(cyclopropyl)methane (5911-08-0) → cyprodime (118111-54-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 16h; Yield given;

DOI:10.1021/jm00122a021

Reference yield:

(-)-N-(cyclopropylmethyl)-4,5α-epoxy-14-methoxymorphinan-6-one (124919-40-0) → cyprodime (118111-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Zn, NH₄Cl / methanol / 0.67 h

2: 67 percent / K₂CO₃ / dimethylformamide / 6.5 h / 80 °C

With potassium carbonate; ammonium chloride; zinc; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

17-(cyclopropylmethyl)-4-hydroxy-14β-methoxymorphinan-6-one

phenyltrimethylammonium chloride

(-)-4,14-dimethoxymorphinan-6-one

chloro(cyclopropyl)methane

Refernces

• 1、 Krassnig, Roland,Schmidhammer, Helmut. "A NEW AND EFFICIENT SYNTHESIS OF THE μ-SELECTIVE OPIOID ANTAGONIST CYPRODIME". . p. 877 - 882. Retrieved 2007/10/02.