4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid

Base Information

• Chemical Name: 4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid
• CAS No.: 104239-97-6
• Molecular Formula: C19H27NO3
• Molecular Weight: 317.428
• European Community (EC) Number: 600-542-3,918-246-0
• UNII: 2E6A626D4R
• DSSTox Substance ID: DTXSID001238002
• Wikidata: Q76414572
• Mol file: 104239-97-6.mol

Synonyms:104239-97-6;4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid;Dutasteride acid;2E6A626D4R;UNII-2E6A626D4R;Finasteride Acid;(5alpha,17beta)-3-Oxo-4-azaandrost-1-ene-17-carboxylic acid;(4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-Dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid;(1S,3aS,3bS,5aR,9aR,9bS,11aS)-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxylic acid;1H-Indeno(5,4-f)quinoline-7-carboxylic acid, 2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-, (4aR,4bS,6aS,7S,9aS,9bS,11aR)-;C19 H27 N O3;MFCD08063794;SCHEMBL1099189;DTXSID001238002;BCP10733;CS-M2829;EX-A1949;AKOS025311234;CS-O-32353;GS-0922;DUTASTERIDE IMPURITY A [EP IMPURITY];O0515;H11005;EN300-20675450;3-Oxo-4-aza-5?-?ndrost-1-ene-17?-carboxylic Acid;3-Oxo-4-aza-5|A-androst-1-ene-17|A-carboxylic acid;4-aza-5|A-androstan-1-ene-3-one-17|A-carboxylic acid;Z3244525813;3-Oxo-4-aza-5alpha-androst-1-ene-17beta-carboxylic acid;(5APHA,17BETA)-3-OXO-4-AZAANDROST-1-ENE-17-CARBOXYLICACID;3-Oxo-4-aza-5 alpha - alpha ndrost-1-ene-17 beta -carboxylic Acid;3-OXO-4-AZA-5.ALPHA.-ANDROST-1-ENE-17.BETA.-CARBOXYLIC ACID;3-Oxo-4-aza-5f inverted question mark-androst-1-ene-17fA-carboxylic Acid;(1S,2R,7R,10S,11S,14S,15S)-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxylic acid;(4aR,4bS,6aS,7S,9aS,9bS,11aR)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxylic Acid;(4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-dimethyl-2-oxo-1H,2H,4aH,4bH,5H,6H,6aH,7H,8H,9H,9aH,9bH,10H,11H,11aH-indeno[5,4-f]quinoline-7-carboxylic acid

Chemical Property of 4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 295-297 °C
• Refractive Index: 1.547
• Boiling Point: 527.3 °C at 760 mmHg
• PKA: 4.80±0.60(Predicted)
• Flash Point: 272.7 °C
• PSA: 66.40000
• Density: 1.166 g/cm³
• LogP: 3.31320
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 317.19909372
• Heavy Atom Count: 23
• Complexity: 585

Purity/Quality:

99% ^*data from raw suppliers

3-Oxo-4-aza-5α-αndrost-1-ene-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)CCC4C3(C=CC(=O)N4)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)O)CC[C@@H]4[C@@]3(C=CC(=O)N4)C
• Uses: 4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid is an intermediate in the synthesis of Finasteride, am onhibitor of 5a-reductase, the enzyme which converts testosterone to the more potent androgen, 5a-dihydrotestosterone A novel intermediate in the synthesis of Finasteride, a 5α-reductase inhibitor used for treatment of benign prostatic hyperplasia acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrogenetic related disorders. A novel intermediate in the synthesis of Finasteride and Dutasteride, a 5α-reductase inhibitors used for treatment of benign prostatic hyperplasia acne, seborrhea, female hirsutism, prostatitis, and p rostatic carcinoma and other hyperandrogenetic related disorders.

Technology Process of 4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid

There total 17 articles about 4-Aza-5a-androstan-1-ene-3-one-17b-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: 85.5%

3-oxo-4-aza-5α-androstane-17β-carboxylic acid (103335-55-3,1430804-94-6) → 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid (104239-97-6)

Guidance literature:

With bis(trimethylsilyl)trifluoroacetamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; 20 deg C, 4 h. then 110 deg C, 18 h.;

DOI:10.1021/ja00218a062

Reference yield:

methyl (2α,5α,17β)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate (149198-45-8) → 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid (104239-97-6)

Guidance literature:

methyl (2α,5α,17β)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate; With potassium tert-butylate; In N,N-dimethyl-formamide; at -15 ℃; for 1.33333h;

With water; In N,N-dimethyl-formamide; at 50 ℃; for 2h;

Reference yield:

2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide (21149-38-2) + 1,3-cylohexanedione (504-02-9) + sodium hydrogensulfite + 3-oxo-4-aza-5α-androstane-17β-carboxylic acid (103335-55-3,1430804-94-6) → 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid (104239-97-6)

Guidance literature:

With hydrogenchloride; bunazosin; In 1,4-dioxane; dichloromethane; acetonitrile;

upstream raw materials:

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

methanol

methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate

dichloromethane

Downstream raw materials:

N-[1-methyl-1-(4-methoxyphenyl)ethyl]-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide

Refernces

• 1、 Guduru, Santhosh,Mutha, V.V.S.R.N. Anji Karun,Vijayabhaskar,Kaliyaperumal, Muralidharan,Achanta, Prabhakar S.,Anugu, Sreenivasa Reddy,Komandla, Bharath,Korupolu, Raghu Babu,Bonige, Kishore Babu,Rumalla, Chidananda Swamy. "Isolation and structural characterization of degradation products of finasteride by preparative HPLC, HRMS and 2D NMR". . p. 1514 - 1518. Retrieved 2019.
• 2、 -. "PROCESS FOR THE SYNTHESIS OF (5α,17β)-N-[(2,5-BIS(TRIFLUOROMETHYL)-PHENYL]-3-OXO-4-AZA-5-ANDROST-1-ENE-17-CARBOXAMIDE". . . Retrieved 2013/03/26.