(1S,2R,3S,4R)-3-{(4-fluorobenzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: (1S,2R,3S,4R)-3-{(4-fluorobenzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester
• CAS No.: 1071520-44-9
• Molecular Formula: C₂₇H₃₁FN₄O₇S₂
• Molecular Weight: 606.696
• Mol file: 1071520-44-9.mol

Synonyms:(1S,2R,3S,4R)-3-{(4-fluorobenzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

Chemical Property of (1S,2R,3S,4R)-3-{(4-fluorobenzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4R)-3-{(4-fluorobenzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

There total 18 articles about (1S,2R,3S,4R)-3-{(4-fluorobenzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 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:

(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[e][1,2,4]thiadiazin-3-yl)-acetic acid (1000313-20-1) + (1S,2R,3S,4R)-3-(4-fluoro-benzylamino)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (1071520-41-6) → (1S,2R,3S,4R)-3-{(4-fluorobenzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (1071520-44-9)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; In N,N-dimethyl-formamide; at 25 ℃; for 12h;

Reference yield:

2-chloro-5-nitrobenzenesulfonamide (96-72-0) → (1S,2R,3S,4R)-3-{(4-fluorobenzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (1071520-44-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / acetonitrile / 20 h / 92 °C / Industry scale

2.1: hydrogen / palladium 10% on activated carbon / ethanol; water; tetrahydrofuran / 43 h / 50 °C / 2844.39 Torr / Industry scale

3.1: pyridine / dichloromethane / 0 - 23 °C / Industry scale

4.1: tetrahydrofuran / 1 h / 0 - 23 °C / Industry scale

5.1: sodium hydroxide; water / 30 h / 23 °C / Industry scale

5.2: 0 °C / Industry scale

6.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 12 h / 25 °C

6.2: pH 1

With pyridine; dmap; water; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

5-nitro-2-chlorobenzenesulfonyl chloride (4533-95-3) → (1S,2R,3S,4R)-3-{(4-fluorobenzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (1071520-44-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: ammonium hydroxide / toluene; water; tetrahydrofuran / 2 h / -10 °C / Reflux

1.2: pH 4

2.1: ammonium hydroxide; ammonium carbonate; copper(II) sulfate / water / 72 h / 118 °C / Autoclave; Industry scale

3.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; methanol / 23 °C / 2585.81 Torr / Industry scale; Autoclave

4.1: pyridine / dichloromethane / 0 - 23 °C / Industry scale

5.1: tetrahydrofuran / 1 h / 0 - 23 °C / Industry scale

6.1: sodium hydroxide; water / 30 h / 23 °C / Industry scale

6.2: 0 °C / Industry scale

7.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 12 h / 25 °C

7.2: pH 1

With pyridine; dmap; ammonium hydroxide; water; hydrogen; ammonium carbonate; copper(II) sulfate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[e][1,2,4]thiadiazin-3-yl)-acetic acid

(1S,2R,3S,4R)-3-(4-fluoro-benzylamino)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

norborn-2-ene

2-chloro-5-nitrobenzenesulfonamide

Downstream raw materials:

N-{3-[(1R,2S,7R,8S)-3-(4-fluoro-benzyl)-6-hydroxy-4-oxo-3-aza-tricyclo[6.2.1.0(2,7)]undec-5-en-5-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}methanesulfonamide

N-{3-[(1R,2S,7R,8S)-3-(4-fluorobenzyl)-6-hydroxy-4-oxo-3-azatricyclo[6.2.1.02,7]undec-5-en-5-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}methanesulfonamide L-arginine salt

N-{3-[(1R,2S,7R,8S)-3-(4-fluorobenzyl)-6-hydroxy-4-oxo-3-azatricyclo[6.2.1.02,7]undec-5-en-5-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}methanesulfonamide L-lysine salt

N-{3-[(1R,2S,7R,8S)-3-(4-fluoro-benzyl)-6-hydroxy-4-oxo-3-aza-tricyclo[6.2.1.0(2,7)]undec-5-en-5-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}methanesulfonamide sodium salt