N-(((5S)-3-(4-(5-(cyanomethylene)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide

Base Information

Chemical Name:N-(((5S)-3-(4-(5-(cyanomethylene)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide
CAS No.:1395323-00-8
Molecular Formula:C₂₁H₂₃FN₄O₃
Molecular Weight:398.437
Hs Code.:

Synonyms:N-(((5S)-3-(4-(5-(cyanomethylene)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N-(((5S)-3-(4-(5-(cyanomethylene)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of N-(((5S)-3-(4-(5-(cyanomethylene)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide

There total 14 articles about N-(((5S)-3-(4-(5-(cyanomethylene)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide 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: 83.0%

: 2537-48-6
diethyl 1-cyanomethylphosphonate

: 1395322-94-7
N-(((5S)-3-(3-fluoro-4-(5-oxohexahydrocyclopenta[c]pyrrol-2(1H)-yl)phenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide

: 1395323-00-8
N-(((5S)-3-(4-(5-(cyanomethylene)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide

Guidance literature:: diethyl 1-cyanomethylphosphonate; With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 1h;

N-(((5S)-3-(3-fluoro-4-(5-oxohexahydrocyclopenta[c]pyrrol-2(1H)-yl)phenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1111/j.1747-0285.2012.01404.x

Reference yield:

: 1395322-86-7
2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole

: 1395323-00-8
N-(((5S)-3-(4-(5-(cyanomethylene)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: toluene-4-sulfonic acid / water; benzene / 3 h / Reflux; Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C

3.1: sodium hydrogencarbonate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

4.2: 12 h / -78 - 20 °C

5.1: triethylamine / dichloromethane / 4 h / 0 - 20 °C

6.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 °C

7.1: pyridine; palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C

8.1: toluene-4-sulfonic acid / water; acetone / 6 h / Reflux

9.1: potassium tert-butylate / tetrahydrofuran / 1 h / -78 °C

9.2: -78 - 20 °C

With pyridine; n-butyllithium; sodium azide; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1111/j.1747-0285.2012.01404.x

Reference yield:

: 1395322-87-8
2-(2-fluoro-4-nitrophenyl)-hexahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]

: 1395323-00-8
N-(((5S)-3-(4-(5-(cyanomethylene)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C

2.1: sodium hydrogencarbonate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

3.2: 12 h / -78 - 20 °C

4.1: triethylamine / dichloromethane / 4 h / 0 - 20 °C

5.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 °C

6.1: pyridine; palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C

7.1: toluene-4-sulfonic acid / water; acetone / 6 h / Reflux

8.1: potassium tert-butylate / tetrahydrofuran / 1 h / -78 °C

8.2: -78 - 20 °C

With pyridine; n-butyllithium; sodium azide; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1111/j.1747-0285.2012.01404.x