(S,E)-N-(1-(1-methyl-2-butylidenehydrazinyl)-1-oxo-3-phenylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide

Base Information

• Chemical Name: (S,E)-N-(1-(1-methyl-2-butylidenehydrazinyl)-1-oxo-3-phenylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide
• CAS No.: 1391931-91-1
• Molecular Formula: C₂₃H₂₇N₃O₄
• Molecular Weight: 409.485

Synonyms:(S,E)-N-(1-(1-methyl-2-butylidenehydrazinyl)-1-oxo-3-phenylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide

Chemical Property of (S,E)-N-(1-(1-methyl-2-butylidenehydrazinyl)-1-oxo-3-phenylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide

Chemical Property:

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Technology Process of (S,E)-N-(1-(1-methyl-2-butylidenehydrazinyl)-1-oxo-3-phenylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide

There total 5 articles about (S,E)-N-(1-(1-methyl-2-butylidenehydrazinyl)-1-oxo-3-phenylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide 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: 87.0%

(S)-N-(1-(1-methylhydrazinyl)-1-oxo-3-phenylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide (1391931-84-2) + butyraldehyde (123-72-8) → (S,E)-N-(1-(1-methyl-2-butylidenehydrazinyl)-1-oxo-3-phenylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide (1391931-91-1)

Guidance literature:

With magnesium sulfate; In tetrahydrofuran; at 25 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.201103322

Reference yield:

(S)-benzyl 2-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)-3-phenylpropanoate (1391931-80-8) → (S,E)-N-(1-(1-methyl-2-butylidenehydrazinyl)-1-oxo-3-phenylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide (1391931-91-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen; acetic acid / ethanol / 2585.81 Torr

2.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1 h / -25 °C / Inert atmosphere

2.2: 24 h / -25 - 25 °C

3.1: magnesium sulfate / tetrahydrofuran / 16 h / 25 °C / Inert atmosphere

With 4-methyl-morpholine; palladium 10% on activated carbon; hydrogen; magnesium sulfate; acetic acid; isobutyl chloroformate; In tetrahydrofuran; ethanol;

DOI:10.1002/chem.201103322

Reference yield:

N-(tert-butoxycarbonyl)-L-phenylalanine benzyl ester (66617-58-1) → (S,E)-N-(1-(1-methyl-2-butylidenehydrazinyl)-1-oxo-3-phenylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide (1391931-91-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 12 h / 0 °C / Inert atmosphere

2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 0 - 25 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen; acetic acid / ethanol / 2585.81 Torr

4.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1 h / -25 °C / Inert atmosphere

4.2: 24 h / -25 - 25 °C

5.1: magnesium sulfate / tetrahydrofuran / 16 h / 25 °C / Inert atmosphere

With 4-methyl-morpholine; hydrogenchloride; palladium 10% on activated carbon; hydrogen; magnesium sulfate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane; ethanol; N,N-dimethyl-formamide;

DOI:10.1002/chem.201103322

upstream raw materials:

(S)-benzyl 2-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)-3-phenylpropanoate

(S)-N-(1-(1-methylhydrazinyl)-1-oxo-3-phenylpropan-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide

butyraldehyde

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

C₂₃H₂₉N₃O₄

(S)-N-[1-(2-butyl-2-cyano-1-methylhydrazinyl)-1-oxo-3-phenylpropan-2-yl]-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide

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