(2S,4S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-4-hydroxy-5-oxopyrrolidine-2-carboxamide

Base Information

Chemical Name:(2S,4S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-4-hydroxy-5-oxopyrrolidine-2-carboxamide
CAS No.:1448347-43-0
Molecular Formula:C₂₉H₂₂ClF₄N₅O₄
Molecular Weight:615.971
Hs Code.:

(2S,4S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-4-hydroxy-5-oxopyrrolidine-2-carboxamide

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Chemical Property of (2S,4S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-4-hydroxy-5-oxopyrrolidine-2-carboxamide

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Technology Process of (2S,4S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-4-hydroxy-5-oxopyrrolidine-2-carboxamide

There total 9 articles about (2S,4S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-4-hydroxy-5-oxopyrrolidine-2-carboxamide 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:

: (2S,4S)-4-((tert-butyldimethylsilyl)oxy)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-5-oxopyrrolidine-2-carboxamide

: 1448347-43-0
(2S,4S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-4-hydroxy-5-oxopyrrolidine-2-carboxamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.333333h;
DOI:10.1021/acsmedchemlett.7b00421

Reference yield:

: 1355328-30-1
N-(3,3-difluorocyclobutyl)formamide

: 1448347-43-0
(2S,4S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-4-hydroxy-5-oxopyrrolidine-2-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine; triphenylphosphine / dichloromethane; tetrachloromethane / 45 °C / Inert atmosphere

2.1: methanol / 0.5 h / 20 °C

2.2: 0.5 h / 20 °C

2.3: 20 °C

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 80 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrabutyl ammonium fluoride; caesium carbonate; triethylamine; triphenylphosphine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; dichloromethane; 2.1: |Ugi Condensation / 2.2: |Ugi Condensation / 2.3: |Ugi Condensation / 3.1: |Buchwald-Hartwig Coupling;
DOI:10.1021/acsmedchemlett.7b00421

Reference yield:

: 367966-67-4
1-(tert-butyl) 2-methyl (2S,4S)-4-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1,2-dicarboxylate

: 1448347-43-0
(2S,4S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-difluorophenyl)-4-hydroxy-5-oxopyrrolidine-2-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C

1.2: 1 h / 20 °C

2.1: methanol / 0.5 h / 20 °C

2.2: 0.5 h / 20 °C

2.3: 20 °C

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 80 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrabutyl ammonium fluoride; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 2.1: |Ugi Condensation / 2.2: |Ugi Condensation / 2.3: |Ugi Condensation / 3.1: |Buchwald-Hartwig Coupling;
DOI:10.1021/acsmedchemlett.7b00421