6-Deschloro-6,7-epoxy Cyproterone Acetate

Base Information

• Chemical Name: 6-Deschloro-6,7-epoxy Cyproterone Acetate
• CAS No.: 15423-97-9
• Molecular Formula: C₂₄H₃₀O₅
• Molecular Weight: 398.499
• European Community (EC) Number: 690-913-6
• UNII: VX2XP7Y34S
• DSSTox Substance ID: DTXSID80540378
• Wikidata: Q76423195
• Mol file: 15423-97-9.mol

Synonyms:6-Deschloro-6,7-epoxy Cyproterone Acetate;15423-97-9;[(1S,2S,3S,5R,9R,11S,12R,13S,16R,17S)-16-acetyl-2,17-dimethyl-6-oxo-10-oxahexacyclo[10.7.0.02,8.03,5.09,11.013,17]nonadec-7-en-16-yl] acetate;VX2XP7Y34S;SCHEMBL10908265;DTXSID80540378;6-Deschloro-6,7-epoxy-cyproterone acetate;CYPROTERONE ACETATE IMPURITY J [EP IMPURITY];(1R,3aS,3bR,3cS,4aR,6aR,7aS,7bS,7cS,9aS)-1-acetyl-7b,9a-dimethyl-6-oxo-1,2,3,3a,3b,3c,4a,6,6a,7,7a,7b,7c,8,9,9a-hexadecahydrocyclopenta[1,2]cyclopropa[5,6]phenanthro[9,10-b]oxiren-1-yl acetate;3'H-Cyclopropa[1,2]pregna-1,4-diene-3,20-dione, 17-(acetyloxy)-6,7-epoxy-1,2-dihydro-, (1beta,2beta,6alpha,7alpha)-;3'H-Cyclopropa[1,2]pregna-1,4-diene-3,20-dione, 6alpha,7alpha-epoxy-1beta,2beta-dihydro-17-hydroxy-, acetate;6alpha,7alpha-epoxy-3,20-dioxo-1beta,2beta-dihydro-3'H-cyclopropa[1,2]pregna-1,4-dien-17-yl acetate

Chemical Property of 6-Deschloro-6,7-epoxy Cyproterone Acetate

Chemical Property:

• PSA: 72.97000
• LogP: 3.25230
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 398.20932405
• Heavy Atom Count: 29
• Complexity: 890

Purity/Quality:

97% ^*data from raw suppliers

6-Deschloro-6,7-epoxy cyproterone acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CCC2C1(CCC3C2C4C(O4)C5=CC(=O)C6CC6C35C)C)OC(=O)C
• Isomeric SMILES: CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H]4[C@H](O4)C5=CC(=O)[C@@H]6C[C@@H]6[C@]35C)C)OC(=O)C
• Uses: An impurity of Cyproterone acetate 6-Deschloro-6,7-epoxy Cyproterone Acetate (Cyproterone Acetate EP Impurity J) is an impurity of Cyproterone acetate (C989100).

Technology Process of 6-Deschloro-6,7-epoxy Cyproterone Acetate

There total 4 articles about 6-Deschloro-6,7-epoxy Cyproterone Acetate 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:

1,2α-methylene-Δ4,6-pregnadiene-17α-ol-3,20-dione-17-acetate (2701-50-0) → 1,2α-methylene-6,7α-oxido-Δ4-pregnen-17α-ol-3,20-dione-17-acetate (15423-97-9)

Guidance literature:

1,2α-methylene-Δ4,6-pregnadiene-17α-ol-3,20-dione-17-acetate; With Perbenzoic acid; In 1,2-dichloro-ethane; at 5 - 20 ℃; for 23h;

With iron(II) sulfate; In dichloromethane; water; 1,2-dichloro-ethane;

With sodium hydrogencarbonate; In dichloromethane; water; 1,2-dichloro-ethane; Product distribution / selectivity;

Reference yield:

1,4,6-triene-3,20-dione-17α-hydroxyprogesterone (66212-25-7) → 1,2α-methylene-6,7α-oxido-Δ4-pregnen-17α-ol-3,20-dione-17-acetate (15423-97-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane

2.1: sodium hydroxide / N,N-dimethyl-formamide / 3 h / 42 - 45 °C

2.2: 2 h / pH 2

3.1: toluene-4-sulfonic acid / chloroform / 58 - 60 °C

4.1: dihydrogen peroxide; phthalic anhydride / ethyl acetate / 8 h / 20 - 30 °C

With phthalic anhydride; dihydrogen peroxide; toluene-4-sulfonic acid; orthoformic acid triethyl ester; sodium hydroxide; In dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

C23H30O4 → 1,2α-methylene-6,7α-oxido-Δ4-pregnen-17α-ol-3,20-dione-17-acetate (15423-97-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / N,N-dimethyl-formamide / 3 h / 42 - 45 °C

1.2: 2 h / pH 2

2.1: toluene-4-sulfonic acid / chloroform / 58 - 60 °C

3.1: dihydrogen peroxide; phthalic anhydride / ethyl acetate / 8 h / 20 - 30 °C

With phthalic anhydride; dihydrogen peroxide; toluene-4-sulfonic acid; sodium hydroxide; In chloroform; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

1,2α-methylene-Δ4,6-pregnadiene-17α-ol-3,20-dione-17-acetate

1,4,6-triene-3,20-dione-17α-hydroxyprogesterone

17α-hydroxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione

Downstream raw materials:

6-chloro-1α-chloromethyl-Δ4,6-pregnadien-17α-ol-3,20-dione-17-acetate

Refernces

• 1、 -. "Further syntheses of cyproterone acetate". Page/Page column 17-18. . Retrieved 2010/02/07.