2-(tert-butoxy)-2-(5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridin-8-yl)acetic acid

Base Information

• Chemical Name: 2-(tert-butoxy)-2-(5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridin-8-yl)acetic acid
• CAS No.: 1428794-30-2
• Molecular Formula: C₃₁H₃₃FN₂O₅
• Molecular Weight: 532.612
• Mol file: 1428794-30-2.mol

Synonyms:2-(tert-butoxy)-2-(5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridin-8-yl)acetic acid

Chemical Property of 2-(tert-butoxy)-2-(5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridin-8-yl)acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(tert-butoxy)-2-(5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridin-8-yl)acetic acid

There total 20 articles about 2-(tert-butoxy)-2-(5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridin-8-yl)acetic 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:

C32H35FN2O5 → 2-(tert-butoxy)-2-(5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridin-8-yl)acetic acid (1428794-30-2)

Guidance literature:

C₃₂H₃₅FN₂O₅; With methanol; lithium hydroxide; at 50 ℃; for 2h;

With hydrogenchloride; In tetrahydrofuran; methanol; water;

Reference yield:

dimethyl 1-(4-fluorobenzyl)-1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-2,3-dicarboxylate (1428795-10-1) → 2-(tert-butoxy)-2-(5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridin-8-yl)acetic acid (1428794-30-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: potassium hydroxide; ethanol / 18 h / 90 °C

2.1: trifluoroacetic anhydride / dichloromethane / 2 h / 20 °C / Cooling with ice

3.1: 2 h / 90 °C / Reflux

4.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.33 h

5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 20 °C / Cooling with ice

5.2: 0 °C

6.1: triethylamine / dichloromethane / 0.25 h / Cooling with ice

7.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 2 h / 80 °C / Inert atmosphere

8.1: lithium hydroxide; methanol / tetrahydrofuran / 18 h / 80 °C / Reflux

8.2: 20 °C

9.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 0.25 h

10.1: sodium tetrahydroborate / 1,2-dimethoxyethane / 1 h / 20 °C / Cooling with ice

10.2: 0 °C

11.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / Cooling with ice

12.1: zinc(II) iodide / dichloromethane / 0.5 h

13.1: hydrogenchloride; water / methanol; 1,4-dioxane / 1 h / 0 °C

14.1: triethylamine; pyridinium p-toluenesulfonate / dichloromethane / 0.75 h

15.1: sodium hydroxide; ethanol / 18 h / 140 °C / Microwave irradiation; Sealed tube

15.2: pH < 2 / Cooling with ice

16.1: methanol; diethyl ether / 0 °C

17.1: perchloric acid / 72 h / 0 °C

18.1: lithium hydroxide; methanol / 2 h / 50 °C

With hydrogenchloride; methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; perchloric acid; oxalyl dichloride; ethanol; water; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; sodium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; HATU; trifluoroacetic anhydride; potassium hydroxide; sodium hydroxide; zinc(II) iodide; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

dimethyl 1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-2,3-dicarboxylate (1428795-11-2) → 2-(tert-butoxy)-2-(5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridin-8-yl)acetic acid (1428794-30-2)

Guidance literature:

Multi-step reaction with 19 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h

2.1: potassium hydroxide; ethanol / 18 h / 90 °C

3.1: trifluoroacetic anhydride / dichloromethane / 2 h / 20 °C / Cooling with ice

4.1: 2 h / 90 °C / Reflux

5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.33 h

6.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 20 °C / Cooling with ice

6.2: 0 °C

7.1: triethylamine / dichloromethane / 0.25 h / Cooling with ice

8.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 2 h / 80 °C / Inert atmosphere

9.1: lithium hydroxide; methanol / tetrahydrofuran / 18 h / 80 °C / Reflux

9.2: 20 °C

10.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 0.25 h

11.1: sodium tetrahydroborate / 1,2-dimethoxyethane / 1 h / 20 °C / Cooling with ice

11.2: 0 °C

12.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / Cooling with ice

13.1: zinc(II) iodide / dichloromethane / 0.5 h

14.1: hydrogenchloride; water / methanol; 1,4-dioxane / 1 h / 0 °C

15.1: triethylamine; pyridinium p-toluenesulfonate / dichloromethane / 0.75 h

16.1: sodium hydroxide; ethanol / 18 h / 140 °C / Microwave irradiation; Sealed tube

16.2: pH < 2 / Cooling with ice

17.1: methanol; diethyl ether / 0 °C

18.1: perchloric acid / 72 h / 0 °C

19.1: lithium hydroxide; methanol / 2 h / 50 °C

With hydrogenchloride; methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; perchloric acid; oxalyl dichloride; ethanol; water; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; sodium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; HATU; trifluoroacetic anhydride; potassium hydroxide; sodium hydroxide; zinc(II) iodide; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

dimethyl 1-(4-fluorobenzyl)-1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-2,3-dicarboxylate

dimethyl 1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-2,3-dicarboxylate

1-(4-fluorobenzyl)-1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-2,3-dicarboxylic acid

methyl 1-(4-fluorobenzyl)-2-((2-methoxy-2-oxoethyl)(methyl)carbamoyl)-1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-3-carboxylate

Refernces