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

Base Information

• Chemical Name: 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
• CAS No.: 1380421-70-4
• Molecular Formula: C₂₄H₃₁NO₇
• Molecular Weight: 445.513

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 3 articles about 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 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: 96.0%

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) → 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 (1380421-70-4)

Guidance literature:

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; With tetramethyl ammoniumhydroxide; In methanol; water; at 20 ℃; for 20h;

With acetic acid; In water; at 20 ℃; pH=5;

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) → 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 (1380421-70-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2.1: tetramethyl ammoniumhydroxide / methanol; water / 20 h / 20 °C

2.2: 20 °C / pH 5

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetramethyl ammoniumhydroxide; potassium bromide; In 1,4-dioxane; methanol; water; 1.1: Suzuki coupling;

DOI:10.1016/j.tetasy.2012.04.008

Reference yield:

(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-[(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 (1380421-70-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2.1: tetramethyl ammoniumhydroxide / methanol; water / 20 h / 20 °C

2.2: 20 °C / pH 5

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetramethyl ammoniumhydroxide; potassium bromide; In 1,4-dioxane; methanol; water; 1.1: 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

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

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

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]-N-(3-(triethoxysilyl)propyl)benzamide

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