3-Oxo-4-aza-5-androstene-17beta-carboxylic acid

Base Information

• Chemical Name: 3-Oxo-4-aza-5-androstene-17beta-carboxylic acid
• CAS No.: 103335-54-2
• Molecular Formula: C19H27NO3
• Molecular Weight: 317.428
• European Community (EC) Number: 407-830-6,600-423-6
• UNII: UCI904SOZG
• DSSTox Substance ID: DTXSID70893628
• Wikidata: Q27291022
• Mol file: 103335-54-2.mol

Synonyms:103335-54-2;3-Oxo-4-aza-5-androstene-17beta-carboxylic acid;UNII-UCI904SOZG;UCI904SOZG;(1S,3aS,3bS,9aR,9bS,11aS)-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,6,8,9,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxylic acid;3-Oxo-4-azaandrost-5-ene-17beta-carboxylic acid;3-OXO-4-AZAANDROST-5-EEN-17-BETA-CARBONZUUR;1H-Indeno(5,4-f)quinoline-7-carboxylic acid, 2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-4a,6a-dimethyl-2-oxo-, (4aR,4bS,6aS,7S,9aS,9bS)-;3-Oxo-4-aza-5-androstene-17.beta.-carboxylic acid;4-Aza-5-androsten-3-one-17-beta-carboxylic acid;SCHEMBL4416881;DTXSID70893628;CS-0008495;3-Oxo-4-aza-5-androstene-17-carboxylic acid;4-aza-5-androsten-3-oxo-17?-carboxylic acid;EC 407-830-6;3-Oxo-4-aza-5-androstene-17|A-carboxylic acid;Q27291022;1H-Indeno[5,4-f]quinoline-7-carboxylicacid,2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-4a,6a-dimethyl-2-oxo-,(4ar,4bs,6as,7s,9as,9bs)-

Chemical Property of 3-Oxo-4-aza-5-androstene-17beta-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >308 °C
• Refractive Index: 1.534
• Boiling Point: 541.405 °C at 760 mmHg
• PKA: 4.79±0.60(Predicted)
• Flash Point: 281.232 °C
• PSA: 66.40000
• Density: 1.214 g/cm³
• LogP: 3.66240
• Solubility.: 1.27 in mg/100g standard fat at 20 ℃
• Water Solubility.: 1.46mg/L
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 317.19909372
• Heavy Atom Count: 23
• Complexity: 597

Purity/Quality:

99.9% ^*data from raw suppliers

3-Oxo-4-aza-5-androstene-17β-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2C(=O)O)CC=C4C3(CCC(=O)N4)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)O)CC=C4[C@@]3(CCC(=O)N4)C
• Uses: 3-Oxo-4-aza-5-androstene-17β-carboxylic Acid is an intermediate used in the synthesis of 5β-Finasteride (F342030), which is an azasteroid and 5β-isomeric impurity of Finasteride (F342000).

Technology Process of 3-Oxo-4-aza-5-androstene-17beta-carboxylic acid

There total 6 articles about 3-Oxo-4-aza-5-androstene-17beta-carboxylic 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: 93.5%

(3S,3aS,5aS,6R,9aS,9bS)-6-(2-carboxyethyl)-3a,6-dimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalene-3-carboxylic acid (76763-14-9) → (4aR,4bS,6aS,7S,9aS,9bS)-4a,6a-dimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid (103335-54-2)

Guidance literature:

With ammonia; In ethylene glycol; at 120 - 140 ℃;

DOI:10.1016/j.bmcl.2011.03.102

Reference yield:

androst-4-en-3-one-17β-carboxylic acid (302-97-6) → (4aR,4bS,6aS,7S,9aS,9bS)-4a,6a-dimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid (103335-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 70.42 percent / aq. Na₂CO₃; NaIO₄; KMnO₄ / 2-methyl-propan-2-ol / 3 h / Heating

2: 81.6 percent / NH₄OAc / acetic acid / 10 h / Heating

With potassium permanganate; sodium periodate; ammonium acetate; sodium carbonate; In acetic acid; tert-butyl alcohol; 1: Ring cleavage / 2: Cyclization;

DOI:10.1016/S0968-0896(99)00169-8

Reference yield:

Pregnenolone (145-13-1) → (4aR,4bS,6aS,7S,9aS,9bS)-4a,6a-dimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid (103335-54-2)

Guidance literature:

Multi-step reaction with 6 steps

1: I₂ / 1.5 h / Heating

2: methanol / 1 h / Heating

3: 70.62 percent / Al(i-PrO)3 / cyclohexanone; toluene / 4 h / Heating

4: 100 percent / aq. KOH / methanol / 5 h / Heating

5: 70.42 percent / aq. Na₂CO₃; NaIO₄; KMnO₄ / 2-methyl-propan-2-ol / 3 h / Heating

6: 81.6 percent / NH₄OAc / acetic acid / 10 h / Heating

With potassium hydroxide; potassium permanganate; sodium periodate; ammonium acetate; iodine; aluminum isopropoxide; sodium carbonate; In methanol; cyclohexanone; acetic acid; toluene; tert-butyl alcohol; 1: Substitution / 2: Substitution / 3: Oxidation / 4: Hydrolysis / 5: Ring cleavage / 6: Cyclization;

DOI:10.1016/S0968-0896(99)00169-8

upstream raw materials:

(3S,3aS,5aS,6R,9aS,9bS)-6-(2-carboxyethyl)-3a,6-dimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalene-3-carboxylic acid

Pregnenolone

methyl 5-androsten-3β-ol-17β-carboxylate

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Downstream raw materials:

3-oxo-4-aza-5α-androstane-17β-carboxylic acid

N-(1,2-diphenylethyl)-3-oxo-4-azaandrost-5-ene-17β-carboxamide

N-(diphenylmethyl)-3-oxo-4-azaandrost-5-ene-17β-carboxamide

N-(1,1-diphenylethyl)-3-oxo-4-azaandrost-5-ene-17β-carboxamide

Refernces

• 1、 Shuang, Zhao,Jiazhen, Wu,Lijuan, Yang,Zhuo, Li,Dahai, Yu,Jinfeng, Li,Jing, Yu,Yongtao, Liang,En-Si, Wang,Xuexun, Fang. "Synthesis and bioactivity of new Finasteride conjugate". supporting information; experimental part. p. 3439 - 3442. Retrieved 2011/07/07.
• 2、 -. "METHOD FOR THE SELECTIVE PREPARATION OF 3-OXO-4-AZA-5A-ANDROSTANE COMPOUND". Page 5-6. . Retrieved 2008/06/13.