5-adamantan-1-yl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)pentanoic acid ethyl ester

Base Information

• Chemical Name: 5-adamantan-1-yl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)pentanoic acid ethyl ester
• CAS No.: 455333-76-3
• Molecular Formula: C₃₅H₃₉O₃P
• Molecular Weight: 538.667

Synonyms:5-adamantan-1-yl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)pentanoic acid ethyl ester

Chemical Property of 5-adamantan-1-yl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)pentanoic acid ethyl ester

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Technology Process of 5-adamantan-1-yl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)pentanoic acid ethyl ester

There total 2 articles about 5-adamantan-1-yl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)pentanoic acid ethyl ester 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: 94.0%

3-(1-adamantyl)propanoic acid (16269-16-2) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → 5-adamantan-1-yl-3-oxo-2-(triphenyl-λ5-phosphanylidene)pentanoic acid ethyl ester (455333-76-3)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 17h;

DOI:10.1021/jm0490686

Reference yield: 79.0%

ethyl (triphenylphosphoranylidene)acetate (1099-45-2) + 3-(1-adamantyl)propanoyl chloride (118550-72-4) → 5-adamantan-1-yl-3-oxo-2-(triphenyl-λ5-phosphanylidene)pentanoic acid ethyl ester (455333-76-3)

Guidance literature:

In benzene; at 20 ℃;

DOI:10.1023/A:1015501313852

Reference yield:

5-adamantan-1-yl-3-oxo-2-(triphenyl-λ5-phosphanylidene)pentanoic acid ethyl ester (455333-76-3) → 3-{[5-(2-adamantan-1-yl-ethyl)-2-tert-butyl-1H-imidazole-4-carbonyl]-amino}-benzoic acid

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / OXONE / tetrahydrofuran / 16 h / 20 °C

2: NH₄OAc; AcOH / 70 °C

3: aq. NaOH / ethanol / Heating

4: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-(dimethylamino)pyridine; 1-hydroxybenzotriazole / dimethylformamide / 20 °C

5: H₂ / Pd/C / tetrahydrofuran; methanol

With dmap; Oxone; sodium hydroxide; ammonium acetate; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm0490686

upstream raw materials:

3-(1-adamantyl)propanoic acid

ethyl (triphenylphosphoranylidene)acetate

3-(1-adamantyl)propanoyl chloride

Downstream raw materials:

5-(2-adamantan-1-yl-ethyl)-2-phenyl-1H-imidazole-4-carboxylic acid

5-(2-adamantan-1-yl-ethyl)-2-phenyl-1H-imidazole-4-carboxylic acid ethyl ester

5-(2-adamantan-1-ylethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid

5-(2-adamantan-1-ylethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid ethyl ester

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