methyl (S)-2,13-dioxo-1¹H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxylate

Base Information

• Chemical Name: methyl (S)-2,13-dioxo-1¹H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxylate
• CAS No.: 1610043-30-5
• Molecular Formula: C₂₁H₂₄N₂O₅
• Molecular Weight: 384.432

Synonyms:methyl (S)-2,13-dioxo-1¹H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxylate

Chemical Property of methyl (S)-2,13-dioxo-1¹H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxylate

Chemical Property:

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Technology Process of methyl (S)-2,13-dioxo-1¹H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxylate

There total 1 articles about methyl (S)-2,13-dioxo-1¹H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxylate 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:

3-(4-hydroxyphenyl)propionic acid methyl ester (5597-50-2) → methyl (S)-2,13-dioxo-11H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxylate (1610043-30-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere

2.1: lithium hydroxide / tetrahydrofuran; water / 3.5 h / 40 °C

3.1: thionyl chloride / dichloromethane / 18.17 h / 0 - 40 °C

4.1: ytterbium(III) triflate / nitromethane / 21 h / 20 °C

5.1: potassium hydroxide / tetrahydrofuran; water / 18 h / 40 - 50 °C

6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

6.2: 18 h / Inert atmosphere

7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 0.5 h / 45 °C / Inert atmosphere

7.2: 18 h / 45 °C / Inert atmosphere

8.1: palladium 10% on activated carbon; hydrogen / dichloromethane / 18 h / 20 °C / 760.05 Torr

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; thionyl chloride; palladium 10% on activated carbon; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hydroxide; lithium hydroxide; ytterbium(III) triflate; In tetrahydrofuran; nitromethane; dichloromethane; water; N,N-dimethyl-formamide; 4.1: |Friedel-Crafts Acylation;

DOI:10.1002/anie.201404301

Reference yield:

methyl (S)-2,13-dioxo-11H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxylate (1610043-30-5) → (S)-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-2,13-dioxo-11H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxamide (1610043-18-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / tetrahydrofuran; water / 18 h / 20 °C

2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

2.2: 18 h / Inert atmosphere

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/anie.201404301

Reference yield:

methyl (S)-2,13-dioxo-11H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxylate (1610043-30-5) → (S)-2,13-dioxo-N-((S)-1-oxo-3-phenylpropan-2-yl)-11H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxamide (1610042-98-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / tetrahydrofuran; water / 18 h / 20 °C

2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

2.2: 18 h / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

With benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/anie.201404301

upstream raw materials:

3-(4-hydroxyphenyl)propionic acid methyl ester

Downstream raw materials:

(S)-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-2,13-dioxo-11H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxamide

(S)-2,13-dioxo-N-((S)-1-oxo-3-phenylpropan-2-yl)-1¹H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxamide

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