(S)-4-[3-(2-amino-3-hydroxypropanoylamino)-4-methoxyphenyl]-6-methoxycoumarin hydrochloride

Base Information

• Chemical Name: (S)-4-[3-(2-amino-3-hydroxypropanoylamino)-4-methoxyphenyl]-6-methoxycoumarin hydrochloride
• CAS No.: 1560773-76-3
• Molecular Formula: C₂₀H₂₀N₂O₆*ClH
• Molecular Weight: 420.85
• Mol file: 1560773-76-3.mol

Synonyms:(S)-4-[3-(2-amino-3-hydroxypropanoylamino)-4-methoxyphenyl]-6-methoxycoumarin hydrochloride

Chemical Property of (S)-4-[3-(2-amino-3-hydroxypropanoylamino)-4-methoxyphenyl]-6-methoxycoumarin hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[3-(2-amino-3-hydroxypropanoylamino)-4-methoxyphenyl]-6-methoxycoumarin hydrochloride

There total 10 articles about (S)-4-[3-(2-amino-3-hydroxypropanoylamino)-4-methoxyphenyl]-6-methoxycoumarin hydrochloride 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: 92.0%

(S)-4-{3-[3-benzyloxy-2-(tert-butoxycarbonylamino)propanoylamino]-4-methoxyphenyl}-6-methoxycoumarin (1560773-64-9) → (S)-4-[3-(2-amino-3-hydroxypropanoylamino)-4-methoxyphenyl]-6-methoxycoumarin hydrochloride (1560773-76-3)

Guidance literature:

(S)-4-{3-[3-benzyloxy-2-(tert-butoxycarbonylamino)propanoylamino]-4-methoxyphenyl}-6-methoxycoumarin; With boron trichloride; In dichloromethane; at -78 ℃; for 4h; Inert atmosphere;

With hydrogenchloride; In ethanol; ethyl acetate; at 50 ℃;

DOI:10.1007/s11172-013-0149-3

Reference yield:

2-(3-tert-butoxycarbonylamino-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (262433-23-8) → (S)-4-[3-(2-amino-3-hydroxypropanoylamino)-4-methoxyphenyl]-6-methoxycoumarin hydrochloride (1560773-76-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 17 h / 20 - 110 °C / Inert atmosphere

2.1: hydrogenchloride; ethanol / ethyl acetate / 50 °C

2.2: 0.5 h / 20 °C

3.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / N,N-dimethyl-formamide / 15 h / 20 - 50 °C / Inert atmosphere

4.1: boron trichloride / dichloromethane / 4 h / -78 °C / Inert atmosphere

4.2: 50 °C

With hydrogenchloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ethanol; boron trichloride; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 1.1: |Suzuki-Miyaura Coupling;

DOI:10.1007/s11172-013-0149-3

Reference yield:

trifluoromethanesulfonic acid 6-methoxy-2-oxo-2H-chromen-4-yl ester (638191-28-3) → (S)-4-[3-(2-amino-3-hydroxypropanoylamino)-4-methoxyphenyl]-6-methoxycoumarin hydrochloride (1560773-76-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 17 h / 20 - 110 °C / Inert atmosphere

2.1: hydrogenchloride; ethanol / ethyl acetate / 50 °C

2.2: 0.5 h / 20 °C

3.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / N,N-dimethyl-formamide / 15 h / 20 - 50 °C / Inert atmosphere

4.1: boron trichloride / dichloromethane / 4 h / -78 °C / Inert atmosphere

4.2: 50 °C

With hydrogenchloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ethanol; boron trichloride; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 1.1: |Suzuki-Miyaura Coupling;

DOI:10.1007/s11172-013-0149-3

upstream raw materials:

2-(3-tert-butoxycarbonylamino-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-iodo-2-nitroanisole

trifluoromethanesulfonic acid 6-methoxy-2-oxo-2H-chromen-4-yl ester

4-hydroxy-6-methoxycoumarin