3-{(E)-[(16E)-3-[2-(benzyloxy)ethyl]-17-oxoestra-1⁽¹⁰⁾,2,4-trien-16-ylidene]methyl}benzamide

Base Information

• Chemical Name: 3-{(E)-[(16E)-3-[2-(benzyloxy)ethyl]-17-oxoestra-1⁽¹⁰⁾,2,4-trien-16-ylidene]methyl}benzamide
• CAS No.: 1318265-24-5
• Molecular Formula: C₃₅H₃₇NO₃
• Molecular Weight: 519.684

Synonyms:3-{(E)-[(16E)-3-[2-(benzyloxy)ethyl]-17-oxoestra-1⁽¹⁰⁾,2,4-trien-16-ylidene]methyl}benzamide

Chemical Property of 3-{(E)-[(16E)-3-[2-(benzyloxy)ethyl]-17-oxoestra-1⁽¹⁰⁾,2,4-trien-16-ylidene]methyl}benzamide

Chemical Property:

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Technology Process of 3-{(E)-[(16E)-3-[2-(benzyloxy)ethyl]-17-oxoestra-1⁽¹⁰⁾,2,4-trien-16-ylidene]methyl}benzamide

There total 5 articles about 3-{(E)-[(16E)-3-[2-(benzyloxy)ethyl]-17-oxoestra-1⁽¹⁰⁾,2,4-trien-16-ylidene]methyl}benzamide 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: 76.0%

3-[2-(benzyloxy)ethyl]estra-1(10),2,4-trien-17-one (1318265-23-4) + 3-carboxamidobenzaldehyde (126534-87-0) → 3-{(E)-[(16E)-3-[2-(benzyloxy)ethyl]-17-oxoestra-1(10),2,4-trien-16-ylidene]methyl}benzamide (1318265-24-5)

Guidance literature:

With water; potassium hydroxide; In ethanol; for 0.5h; Reflux;

Reference yield:

(8R,9S,13S,14S)-13-methyl-3-vinyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolane] (1318265-21-2) → 3-{(E)-[(16E)-3-[2-(benzyloxy)ethyl]-17-oxoestra-1(10),2,4-trien-16-ylidene]methyl}benzamide (1318265-24-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 16 h / -78 - 20 °C / Inert atmosphere

1.2: 3 h / 0 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

2.2: 17 h / 0 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / water; acetone / 5 h / 20 °C

4.1: potassium hydroxide / ethanol; water / 0.5 h / Reflux

With hydrogenchloride; dimethylsulfide borane complex; sodium hydride; potassium hydroxide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetone; mineral oil;

DOI:10.1021/ml200093v

Reference yield:

3-(2-hydroxyethyl)estra-1(10),2,4-trien-17-dioxolane (1318265-22-3) → 3-{(E)-[(16E)-3-[2-(benzyloxy)ethyl]-17-oxoestra-1(10),2,4-trien-16-ylidene]methyl}benzamide (1318265-24-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

1.2: 17 h / 0 - 20 °C / Inert atmosphere

2.1: hydrogenchloride / water; acetone / 5 h / 20 °C

3.1: potassium hydroxide / ethanol; water / 0.5 h / Reflux

With hydrogenchloride; sodium hydride; potassium hydroxide; In ethanol; water; N,N-dimethyl-formamide; acetone; mineral oil;

DOI:10.1021/ml200093v

upstream raw materials:

(8R,9S,13S,14S)-13-methyl-3-vinyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolane]

3-(2-hydroxyethyl)estra-1⁽¹⁰⁾,2,4-trien-17-dioxolane

3-[2-(benzyloxy)ethyl]estra-1⁽¹⁰⁾,2,4-trien-17-one

3-carboxamidobenzaldehyde

Downstream raw materials:

3-{(E)-[(16E,17β)-3-[2-(benzyloxy)ethyl]-17-hydroxyestra-1,3,5(10)-trien-16-ylidene]methyl}benzamide

3-{[(16β,17β)-17-hydroxy-3-(2-hydroxyethyl)estra-1,3,5(10)-trien-16-yl]methyl}benzamide

3-{[(16β,17β)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide

3-{[(16β,17β)-3-(2-chloroethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide

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