2-Bromo-N-[2-[4-(3,17beta-dihydroxyestra-1,3,5⁽¹⁰⁾-trien-11beta-yl)phenoxy]ethyl]-N-methylacetamide

Base Information

• Chemical Name: 2-Bromo-N-[2-[4-(3,17beta-dihydroxyestra-1,3,5⁽¹⁰⁾-trien-11beta-yl)phenoxy]ethyl]-N-methylacetamide
• CAS No.: 261718-56-3
• Molecular Formula: C₂₉H₃₆BrNO₄
• Molecular Weight: 542.513

Synonyms:2-Bromo-N-[2-[4-(3,17beta-dihydroxyestra-1,3,5⁽¹⁰⁾-trien-11beta-yl)phenoxy]ethyl]-N-methylacetamide

Chemical Property of 2-Bromo-N-[2-[4-(3,17beta-dihydroxyestra-1,3,5⁽¹⁰⁾-trien-11beta-yl)phenoxy]ethyl]-N-methylacetamide

Chemical Property:

Purity/Quality:

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Technology Process of 2-Bromo-N-[2-[4-(3,17beta-dihydroxyestra-1,3,5⁽¹⁰⁾-trien-11beta-yl)phenoxy]ethyl]-N-methylacetamide

There total 11 articles about 2-Bromo-N-[2-[4-(3,17beta-dihydroxyestra-1,3,5⁽¹⁰⁾-trien-11beta-yl)phenoxy]ethyl]-N-methylacetamide 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: 85.0%

2-bromo-N-methyl-N-(2-{4-[13-methyl-3,17-bis-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-11-yl]-phenoxy}-ethyl)-acetamide → 2-Bromo-N-[2-[4-(3,17beta-dihydroxyestra-1,3,5(10)-trien-11beta-yl)phenoxy]ethyl]-N-methylacetamide (261718-56-3)

Guidance literature:

With hydrogen bromide; In tetrahydrofuran; methanol; at 20 ℃; for 1.5h;

DOI:10.1021/jm990179s

Reference yield:

11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione (134414-14-5) → 2-Bromo-N-[2-[4-(3,17beta-dihydroxyestra-1,3,5(10)-trien-11beta-yl)phenoxy]ethyl]-N-methylacetamide (261718-56-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaH / dimethylformamide / 0.42 h

1.2: dimethylformamide / 22 h / 20 °C

2.1: 57 percent / 6 N aq. HCl / dimethylformamide / 1 h / 20 °C

3.1: 98 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

4.1: AcBr; Ac₂O / CH₂Cl₂ / 1.5 h / 0 - 20 °C

4.2: 74 percent / 2 N aq. NaOH / methanol; tetrahydrofuran / 0.75 h / 20 °C

5.1: 88 percent / NaBH₄ / methanol; tetrahydrofuran / 1 h / 0 °C

6.1: 72 percent / NaI / butan-2-one / 17 h / Heating

7.1: 86 percent / p-toluenosulfonic acid / tetrahydrofuran / 1.5 h

8.1: NaH / tetrahydrofuran / 0.33 h

8.2: 49 percent / dimethylformamide; tetrahydrofuran / 2 h / 80 °C

9.1: 100 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / 20 °C

10.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

11.1: 85 percent / 2 N aq. HBr / methanol; tetrahydrofuran / 1.5 h / 20 °C

With pyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; Acetyl bromide; hydrogen bromide; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; triethylamine; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; butanone; 1.1: deprotonation / 1.2: Alkylation / 2.1: desilylation / 3.1: mesylation / 4.1: Aromatization / 4.2: Hydrolysis / 5.1: Reduction / 6.1: Iodination / 7.1: Etherification / 8.1: deprotonation / 8.2: Substitution / 9.1: Hydrolysis / 10.1: Acylation / 11.1: Hydrolysis;

DOI:10.1021/jm990179s

Reference yield:

11beta-[4-(2-Iodoethoxy)phenyl]estra-1,3,5(10)-triene-3,17beta-diol (253169-45-8) → 2-Bromo-N-[2-[4-(3,17beta-dihydroxyestra-1,3,5(10)-trien-11beta-yl)phenoxy]ethyl]-N-methylacetamide (261718-56-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 86 percent / p-toluenosulfonic acid / tetrahydrofuran / 1.5 h

2.1: NaH / tetrahydrofuran / 0.33 h

2.2: 49 percent / dimethylformamide; tetrahydrofuran / 2 h / 80 °C

3.1: 100 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / 20 °C

4.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

5.1: 85 percent / 2 N aq. HBr / methanol; tetrahydrofuran / 1.5 h / 20 °C

With pyridine; sodium hydroxide; hydrogen bromide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; 1.1: Etherification / 2.1: deprotonation / 2.2: Substitution / 3.1: Hydrolysis / 4.1: Acylation / 5.1: Hydrolysis;

DOI:10.1021/jm990179s

upstream raw materials:

11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione

11beta-[4-(2-Iodoethoxy)phenyl]estra-1,3,5⁽¹⁰⁾-triene-3,17beta-diol

11β-[4-(2-hydroxyethoxy)phenyl]estra-4,9-diene-3,17-dione

2-[4-(3-hydroxy-3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)phenoxy]ethyl methanesulfonate

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