((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-[(2R,3R)-3-(4-fluoro-phenyl)-aziridin-2-yl]-methanone

Base Information

• Chemical Name: ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-[(2R,3R)-3-(4-fluoro-phenyl)-aziridin-2-yl]-methanone
• CAS No.: 654054-26-9
• Molecular Formula: C₁₉H₂₃FN₂O₃S
• Molecular Weight: 378.468

Synonyms:((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-[(2R,3R)-3-(4-fluoro-phenyl)-aziridin-2-yl]-methanone

Chemical Property of ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-[(2R,3R)-3-(4-fluoro-phenyl)-aziridin-2-yl]-methanone

Chemical Property:

Purity/Quality:

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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-[(2R,3R)-3-(4-fluoro-phenyl)-aziridin-2-yl]-methanone

There total 1 articles about ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-[(2R,3R)-3-(4-fluoro-phenyl)-aziridin-2-yl]-methanone 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: 96.0%

((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-[(2R,3R)-1-diphenylphosphanyl-3-(4-fluoro-phenyl)-aziridin-2-yl]-methanone → ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-[(2R,3R)-3-(4-fluoro-phenyl)-aziridin-2-yl]-methanone (654054-26-9)

Guidance literature:

With boron trifluoride diethyl etherate; In methanol; dichloromethane;

DOI:10.1055/s-2003-41470

Reference yield: 67.0%

((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-[(2R,3R)-3-(4-fluoro-phenyl)-aziridin-2-yl]-methanone (654054-26-9) → (R)-2-Amino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-(4-fluoro-phenyl)-propan-1-one (654054-42-9)

Guidance literature:

With hydrogen; trifluoroacetic acid; palladium dihydroxide; In methanol; ethyl acetate; at 20 ℃; for 14h; atmospheric pressure;

DOI:10.1055/s-2003-41470

Reference yield:

((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-[(2R,3R)-3-(4-fluoro-phenyl)-aziridin-2-yl]-methanone (654054-26-9) → (R)-4-fluorophenylalanine (18125-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / H₂; aq. TFA / Pd(OH)2 / ethyl acetate; methanol / 14 h / 20 °C / atmospheric pressure

2: 92 percent / aq. LiOH / tetrahydrofuran / 20 °C

With lithium hydroxide; hydrogen; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethyl acetate;

DOI:10.1055/s-2003-41470

Downstream raw materials:

(R)-2-Amino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(4-fluoro-phenyl)-propan-1-one

(R)-4-fluorophenylalanine

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