3-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile

Base Information

• Chemical Name: 3-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile
• CAS No.: 203512-44-1
• Molecular Formula: C₂₀H₂₂N₂O₃S
• Molecular Weight: 370.472

Synonyms:3-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile

Chemical Property of 3-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile

Chemical Property:

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Technology Process of 3-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile

There total 1 articles about 3-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile 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: 70.0%

3-(3-cyano-phenyl)-acrylic acid methyl ester (193151-10-9) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → 3-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile (203512-44-1)

Guidance literature:

With trimethylaluminum; In toluene;

DOI:10.1016/S0960-894X(99)00164-X

Reference yield:

3-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile (203512-44-1) → (3S,4R)-1-[(2'-tert-butylaminosulfonyl-[1,1']-biphenyl-4-yl)methyl]-4-(3-cyanophenyl)pyrrolidin-3-ylcarboxylic acid (203512-47-4)

Guidance literature:

Multi-step reaction with 3 steps

1: TFA / CH₂Cl₂

2: (Ph₃P)4Pd, aq. Na₂CO₃ / benzene / 80 °C

3: aq. LiOH / tetrahydrofuran

With lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0960-894X(99)00164-X

Reference yield:

3-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile (203512-44-1) → (3S,4R)-1-(2'-tert-Butylsulfamoyl-biphenyl-4-ylmethyl)-4-(3-carbamimidoyl-phenyl)-pyrrolidine-3-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: TFA / CH₂Cl₂

2: (Ph₃P)4Pd, aq. Na₂CO₃ / benzene / 80 °C

3: aq. LiOH / tetrahydrofuran

4: HCl / 0 °C

5: (NH₄)2CO₃ / methanol

With hydrogenchloride; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium carbonate; sodium carbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/S0960-894X(99)00164-X

upstream raw materials:

3-(3-cyano-phenyl)-acrylic acid methyl ester

(2R)-bornane-10,2-sultam

Downstream raw materials:

3-[(3R,4S)-1-(4-Bromo-benzyl)-4-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-pyrrolidin-3-yl]-benzonitrile

(3S,4R)-1-[(2'-tert-butylaminosulfonyl-[1,1']-biphenyl-4-yl)methyl]-4-(3-cyanophenyl)pyrrolidin-3-ylcarboxylic acid

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