methyl 4-[(4S,14S)-()-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-trien-19-yl]-benzoate

Base Information

• Chemical Name: methyl 4-[(4S,14S)-()-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-trien-19-yl]-benzoate
• CAS No.: 1380421-69-1
• Molecular Formula: C₂₅H₃₃NO₇
• Molecular Weight: 459.54

Synonyms:methyl 4-[(4S,14S)-()-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-trien-19-yl]-benzoate

Chemical Property of methyl 4-[(4S,14S)-()-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-trien-19-yl]-benzoate

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Technology Process of methyl 4-[(4S,14S)-()-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-trien-19-yl]-benzoate

There total 3 articles about methyl 4-[(4S,14S)-()-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-trien-19-yl]-benzoate 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%

(4S,14S)-(+)-19-iodo-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-triene (1380421-68-0) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → methyl 4-[(4S,14S)-()-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-trien-19-yl]-benzoate (1380421-69-1)

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium bromide; In 1,4-dioxane; at 85 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.04.008

Reference yield: 69.0%

(4S,14S)-(+)-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-trien-19-yl trifluoromethanesulfonate (1380421-67-9) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → methyl 4-[(4S,14S)-()-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-trien-19-yl]-benzoate (1380421-69-1)

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium bromide; In 1,4-dioxane; at 85 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.04.008

Reference yield:

(4S,14S)-(+)-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-trien-19-yl trifluoromethanesulfonate (1380421-67-9) → methyl 4-[(4S,14S)-()-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-trien-19-yl]-benzoate (1380421-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; sodium iodide / water; acetonitrile / 5 h / 20 °C

2: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium bromide / 1,4-dioxane / 5 h / 85 °C / Inert atmosphere

With hydrogenchloride; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium iodide; potassium bromide; In 1,4-dioxane; water; acetonitrile; 2: Suzuki coupling;

DOI:10.1016/j.tetasy.2012.04.008

upstream raw materials:

(4S,14S)-(+)-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-trien-19-yl trifluoromethanesulfonate

4-methoxycarbonylphenylboronic acid

(4S,14S)-(+)-19-iodo-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene

Downstream raw materials:

4-[(4S,14S)-(+)-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-trien-19-yl]benzoic acid

4-[(4S,14S)-(-)-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1⁽²¹⁾,17,19-trien-19-yl]-N-(3-(triethoxysilyl)propyl)benzamide

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