(4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-19-oxo-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,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-19-oxo-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]-nonadeca-1⁽¹⁹⁾,15,17-trien-11-one
• CAS No.: 1350538-43-0
• Molecular Formula: C₃₄H₃₄N₆O₁₀S₂
• Molecular Weight: 750.81

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

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

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

There total 9 articles about (4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-19-oxo-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: 94.0%

(S)-2-(2-nitrophenylsulfonamido)-N-((1R,2R)-2-(2-nitrophenylsulfonamido)cyclohexyl)-3-phenylpropanamide (1350538-34-9) + 2,6-bis(chloromethyl)pyridine-N-oxide (201160-41-0) → (4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-19-oxo-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]-nonadeca-1(19),15,17-trien-11-one (1350538-43-0)

Guidance literature:

(S)-2-(2-nitrophenylsulfonamido)-N-((1R,2R)-2-(2-nitrophenylsulfonamido)cyclohexyl)-3-phenylpropanamide; With potassium carbonate; In acetonitrile; Reflux;

2,6-bis(chloromethyl)pyridine-N-oxide; With potassium iodide; In acetonitrile; for 3h; Reflux;

DOI:10.3987/COM-11-12249

Reference yield:

2-Nitrobenzenesulfonyl chloride (1694-92-4) → (4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-19-oxo-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]-nonadeca-1(19),15,17-trien-11-one (1350538-43-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / water / 17 h / 60 - 70 °C

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

3.1: potassium carbonate / acetonitrile / Reflux

3.2: 3 h / Reflux

With dmap; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; water; acetonitrile;

DOI:10.3987/COM-11-12249

Reference yield:

2,6-bis(chloromethyl)pyridine (3099-28-3) → (4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-19-oxo-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]-nonadeca-1(19),15,17-trien-11-one (1350538-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dihydrogen peroxide; acetic acid / water / 5 h / 70 °C

2.1: potassium carbonate / acetonitrile / Reflux

2.2: 3 h / Reflux

With dihydrogen peroxide; potassium carbonate; acetic acid; In water; acetonitrile;

DOI:10.3987/COM-11-12249

upstream raw materials:

2,6-bis(chloromethyl)pyridine

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

2,6-bis(chloromethyl)pyridine-N-oxide

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

Downstream raw materials:

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

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