<9S-(9R*,12R*,15R*)>-methyl 15--4-methoxy-12-<(4-methoxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-9-carboxylate

Base Information

• Chemical Name: <9S-(9R*,12R*,15R*)>-methyl 15--4-methoxy-12-<(4-methoxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-9-carboxylate
• CAS No.: 112920-92-0
• Molecular Formula: C₃₂H₃₅N₃O₈
• Molecular Weight: 589.645
• Mol file: 112920-92-0.mol

Synonyms:

Chemical Property of <9S-(9R*,12R*,15R*)>-methyl 15--4-methoxy-12-<(4-methoxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-9-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <9S-(9R*,12R*,15R*)>-methyl 15--4-methoxy-12-<(4-methoxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-9-carboxylate

There total 19 articles about <9S-(9R*,12R*,15R*)>-methyl 15--4-methoxy-12-<(4-methoxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-9-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:

(E/Z)-tert-butyl 3-hydroxy-4-methoxycinnamate (118459-78-2,118459-93-1) → <9S-(9R*,12R*,15R*)>-methyl 15--4-methoxy-12-<(4-methoxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene-9-carboxylate (112920-92-0,118493-33-7)

Guidance literature:

Multi-step reaction with 19 steps

1: 91 percent / K₂CO₃, CuO / pyridine / 24 h / 145 °C

2: H₂ / 10percent Pd/C / ethanol; acetic acid / 10 h

3: Et₃N / tetrahydrofuran / 1.) 78 deg C, 15 min; 2.) 0 deg C, 45 min

4: 1.) n-BuLi / 1.) hexane, THF, -78 deg C; 2.) hexane, THF, -78 deg C, 15 min and then to room temp., 1.5 h

5: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 15 min, 2.) THF, toluene, -78 deg C, 2 min

6: 1.) titanium tetraisopropoxide / 2.) 70 deg C, 2 h

7: H₂ / Raney Ni / CH₂Cl₂; acetic acid / 6.5 h

8: trifluoroacetic acid, thioanisole / CH₂Cl₂ / 1 h / 0 deg C --> room temp.

10: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

11: 1.) n-BuLi / 1.) THF, hexanes, 2.) -78 deg C, 20 min

12: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 20 min; 2.) THF, toluene, -78 deg C, 1.5 min

13: aq. LiOOH / tetrahydrofuran / 1 h / 0 °C

14: diethyl ether / 0.25 h

15: H₂ / 10percent Pd/C / diethyl ether; methanol; acetic acid / 0.5 h

16: NaHCO₃ / H₂O; dioxane / 3 h / Ambient temperature

17: 93 percent / diisopropylcarbodiimide / tetrahydrofuran / 1.) 0 deg C, 2 h; 2.) room temp., 15 h

18: 67 percent / H₂, N-methylmorpholine / Pd⁽⁰⁾ / ethanol; dioxane / 7 h / 90 °C

19: 1.) trifluoroacetic acid, thioanisole; 2.) pyridine / 1.) CH₂Cl₂, 0 deg C, 15 min --> room temp., 1.5 h; 2.) room temp., 1 h

With 4-methyl-morpholine; pyridine; titanium(IV) isopropylate; n-butyllithium; lithium hydroperoxide; methyl-phenyl-thioether; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; triethylamine; trifluoroacetic acid; copper(II) oxide; diisopropyl-carbodiimide; palladium on activated charcoal; nickel; palladium; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid;

DOI:10.1021/ja00185a042

Reference yield:

3-{4-[5-(2-tert-Butoxycarbonyl-ethyl)-2-methoxy-phenoxy]-phenyl}-propionic acid (118459-95-3) → <9S-(9R*,12R*,15R*)>-methyl 15--4-methoxy-12-<(4-methoxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene-9-carboxylate (112920-92-0,118493-33-7)

Guidance literature:

Multi-step reaction with 17 steps

1: Et₃N / tetrahydrofuran / 1.) 78 deg C, 15 min; 2.) 0 deg C, 45 min

2: 1.) n-BuLi / 1.) hexane, THF, -78 deg C; 2.) hexane, THF, -78 deg C, 15 min and then to room temp., 1.5 h

3: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 15 min, 2.) THF, toluene, -78 deg C, 2 min

4: 1.) titanium tetraisopropoxide / 2.) 70 deg C, 2 h

5: H₂ / Raney Ni / CH₂Cl₂; acetic acid / 6.5 h

6: trifluoroacetic acid, thioanisole / CH₂Cl₂ / 1 h / 0 deg C --> room temp.

8: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

9: 1.) n-BuLi / 1.) THF, hexanes, 2.) -78 deg C, 20 min

10: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 20 min; 2.) THF, toluene, -78 deg C, 1.5 min

11: aq. LiOOH / tetrahydrofuran / 1 h / 0 °C

12: diethyl ether / 0.25 h

13: H₂ / 10percent Pd/C / diethyl ether; methanol; acetic acid / 0.5 h

14: NaHCO₃ / H₂O; dioxane / 3 h / Ambient temperature

15: 93 percent / diisopropylcarbodiimide / tetrahydrofuran / 1.) 0 deg C, 2 h; 2.) room temp., 15 h

16: 67 percent / H₂, N-methylmorpholine / Pd⁽⁰⁾ / ethanol; dioxane / 7 h / 90 °C

17: 1.) trifluoroacetic acid, thioanisole; 2.) pyridine / 1.) CH₂Cl₂, 0 deg C, 15 min --> room temp., 1.5 h; 2.) room temp., 1 h

With 4-methyl-morpholine; pyridine; titanium(IV) isopropylate; n-butyllithium; lithium hydroperoxide; methyl-phenyl-thioether; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; diisopropyl-carbodiimide; palladium on activated charcoal; nickel; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid;

DOI:10.1021/ja00185a042

Reference yield:

C28H36O7 → <9S-(9R*,12R*,15R*)>-methyl 15--4-methoxy-12-<(4-methoxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene-9-carboxylate (112920-92-0,118493-33-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) n-BuLi / 1.) hexane, THF, -78 deg C; 2.) hexane, THF, -78 deg C, 15 min and then to room temp., 1.5 h

2: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 15 min, 2.) THF, toluene, -78 deg C, 2 min

3: 1.) titanium tetraisopropoxide / 2.) 70 deg C, 2 h

4: H₂ / Raney Ni / CH₂Cl₂; acetic acid / 6.5 h

5: trifluoroacetic acid, thioanisole / CH₂Cl₂ / 1 h / 0 deg C --> room temp.

7: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

8: 1.) n-BuLi / 1.) THF, hexanes, 2.) -78 deg C, 20 min

9: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 20 min; 2.) THF, toluene, -78 deg C, 1.5 min

10: aq. LiOOH / tetrahydrofuran / 1 h / 0 °C

11: diethyl ether / 0.25 h

12: H₂ / 10percent Pd/C / diethyl ether; methanol; acetic acid / 0.5 h

13: NaHCO₃ / H₂O; dioxane / 3 h / Ambient temperature

14: 93 percent / diisopropylcarbodiimide / tetrahydrofuran / 1.) 0 deg C, 2 h; 2.) room temp., 15 h

15: 67 percent / H₂, N-methylmorpholine / Pd⁽⁰⁾ / ethanol; dioxane / 7 h / 90 °C

16: 1.) trifluoroacetic acid, thioanisole; 2.) pyridine / 1.) CH₂Cl₂, 0 deg C, 15 min --> room temp., 1.5 h; 2.) room temp., 1 h

With 4-methyl-morpholine; pyridine; titanium(IV) isopropylate; n-butyllithium; lithium hydroperoxide; methyl-phenyl-thioether; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; diisopropyl-carbodiimide; palladium on activated charcoal; nickel; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid;

DOI:10.1021/ja00185a042

upstream raw materials:

acetic anhydride

(E/Z)-tert-butyl 3-hydroxy-4-methoxycinnamate

3-{4-[5-(2-tert-Butoxycarbonyl-ethyl)-2-methoxy-phenoxy]-phenyl}-propionic acid

(S)-2-Amino-3-{4-[5-(2-carboxy-ethyl)-2-methoxy-phenoxy]-phenyl}-propionic acid benzyl ester

Downstream raw materials:

K-13

Refernces