17a-aza-17a-benzyl-17-oxo-17a-homoandrosta-3,5-dien-3-oic acid

Base Information

• Chemical Name: 17a-aza-17a-benzyl-17-oxo-17a-homoandrosta-3,5-dien-3-oic acid
• CAS No.: 1393748-68-9
• Molecular Formula: C₂₇H₃₃NO₃
• Molecular Weight: 419.564
• Mol file: 1393748-68-9.mol

Synonyms:17a-aza-17a-benzyl-17-oxo-17a-homoandrosta-3,5-dien-3-oic acid

Chemical Property of 17a-aza-17a-benzyl-17-oxo-17a-homoandrosta-3,5-dien-3-oic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 17a-aza-17a-benzyl-17-oxo-17a-homoandrosta-3,5-dien-3-oic acid

There total 7 articles about 17a-aza-17a-benzyl-17-oxo-17a-homoandrosta-3,5-dien-3-oic acid 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: 60.9%

17a-aza-17a-benzyl-3-cyano-17a-homoandrosta-3,5-dien-17-one (1393748-59-8) → 17a-aza-17a-benzyl-17-oxo-17a-homoandrosta-3,5-dien-3-oic acid (1393748-68-9)

Guidance literature:

17a-aza-17a-benzyl-3-cyano-17a-homoandrosta-3,5-dien-17-one; With sodium hydroxide; In ethanol; water; for 24h; Reflux;

With hydrogenchloride; In ethanol; dichloromethane; water; at 50 ℃; pH=1.5 - 2;

DOI:10.1016/j.ejmech.2012.06.026

Reference yield:

3β-acetoxy-androst-5-en-17-one oxime (84368-89-8,106294-20-6,119907-02-7,21063-30-9) → 17a-aza-17a-benzyl-17-oxo-17a-homoandrosta-3,5-dien-3-oic acid (1393748-68-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: thionyl chloride / 1,4-dioxane; benzene / 0.33 h / 15 - 20 °C

2.1: potassium hydroxide / methanol / 1.17 h / Reflux

3.1: cyclohexanone; aluminum isopropoxide / 1,4-dioxane; toluene / 5 h / Reflux

4.1: phosphorus tribromide; acetic acid / 24 h / 8 - 10 °C

5.1: N,N-dimethyl-formamide / 5 h / Reflux

6.1: sodium hydride / tetrahydrofuran / 0.17 h

6.2: 24 h / 20 °C

7.1: sodium hydroxide / ethanol; water / 24 h / Reflux

7.2: 50 °C / pH 1.5 - 2

With thionyl chloride; cyclohexanone; phosphorus tribromide; aluminum isopropoxide; sodium hydride; acetic acid; potassium hydroxide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; toluene; benzene; 1.1: Beckmann rearrangement / 3.1: Oppenauer oxidation;

DOI:10.1016/j.ejmech.2012.06.026

Reference yield:

(10aR,12aS)-10a,12a-dimethyl-4,4a,4b,5,6,9,10,10a,10b,11,12,12a-dodecahydronaphtho[2,1-f]quinoline-2,8(1H,3H)-dione (1600-81-3) → 17a-aza-17a-benzyl-17-oxo-17a-homoandrosta-3,5-dien-3-oic acid (1393748-68-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: phosphorus tribromide; acetic acid / 24 h / 8 - 10 °C

2.1: N,N-dimethyl-formamide / 5 h / Reflux

3.1: sodium hydride / tetrahydrofuran / 0.17 h

3.2: 24 h / 20 °C

4.1: sodium hydroxide / ethanol; water / 24 h / Reflux

4.2: 50 °C / pH 1.5 - 2

With phosphorus tribromide; sodium hydride; acetic acid; sodium hydroxide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2012.06.026

upstream raw materials:

17a-aza-17a-benzyl-3-cyano-17a-homoandrosta-3,5-dien-17-one

17a-aza-3-bromo-17a-homoandrosta-3,5-dien-17-one

17a-aza-3-cyano-17a-homoandrosta-3,5-dien-17-one

prasterone acetate

Refernces