(4R,9R)-12-benzyl-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1⁽¹⁹⁾,15,17-trien-11-one

Base Information

• Chemical Name: (4R,9R)-12-benzyl-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1⁽¹⁹⁾,15,17-trien-11-one
• CAS No.: 1350538-40-7
• Molecular Formula: C₂₂H₂₈N₄O
• Molecular Weight: 364.491

Synonyms:(4R,9R)-12-benzyl-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1⁽¹⁹⁾,15,17-trien-11-one

Chemical Property of (4R,9R)-12-benzyl-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1⁽¹⁹⁾,15,17-trien-11-one

Chemical Property:

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Technology Process of (4R,9R)-12-benzyl-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1⁽¹⁹⁾,15,17-trien-11-one

There total 8 articles about (4R,9R)-12-benzyl-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1⁽¹⁹⁾,15,17-trien-11-one 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: 84.0%

(4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1(19),15,17-trien-11-one (1350538-37-2) → (4R,9R)-12-benzyl-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1(19),15,17-trien-11-one (1350538-40-7)

Guidance literature:

With potassium carbonate; thiophenol; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.3987/COM-11-12249

Reference yield:

(S)-2-(2-nitrophenylsulfonamido)-N-((1R,2R)-2-(2-nitrophenylsulfonamido)cyclohexyl)-3-phenylpropanamide (1350538-34-9) → (4R,9R)-12-benzyl-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1(19),15,17-trien-11-one (1350538-40-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 90 °C

1.2: 3 h / Reflux

2.1: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 2 h / 20 °C

With potassium carbonate; thiophenol; In N,N-dimethyl-formamide; 1.2: Richman-Atkins cyclization;

DOI:10.3987/COM-11-12249

Reference yield:

trans-1,2-(R,R)-diammoniumcyclohexane tartrate (32044-22-7,39961-95-0) → (4R,9R)-12-benzyl-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1(19),15,17-trien-11-one (1350538-40-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine; sodium hydroxide / dichloromethane / 0.17 h / 0 °C

2.1: dichloromethane / 3.5 h / 0 - 20 °C

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 17 h / 0 - 20 °C

4.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 90 °C

4.2: 3 h / Reflux

5.1: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 2 h / 20 °C

With dmap; potassium carbonate; thiophenol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4.2: Richman-Atkins cyclization;

DOI:10.3987/COM-11-12249

upstream raw materials:

(S)-2-(2-nitrophenylsulfonamido)-N-((1R,2R)-2-(2-nitrophenylsulfonamido)cyclohexyl)-3-phenylpropanamide

(4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1⁽¹⁹⁾,15,17-trien-11-one

N-(2-aminocyclohexyl)-2-nitrobenzene-1-sulfonamide

trans-1,2-(R,R)-diammoniumcyclohexane tartrate

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