(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

Base Information

• Chemical Name: (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
• CAS No.: 654054-42-9
• Molecular Formula: C₁₉H₂₅FN₂O₃S
• Molecular Weight: 380.484

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Safty Information:

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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (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

There total 2 articles about (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 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: 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)-1-diphenylphosphanyl-3-(4-fluoro-phenyl)-aziridin-2-yl]-methanone → (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:

Multi-step reaction with 2 steps

1: 96 percent / BF₃*OEt₂ / CH₂Cl₂; methanol

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

With boron trifluoride diethyl etherate; hydrogen; trifluoroacetic acid; palladium dihydroxide; In methanol; dichloromethane; ethyl acetate;

DOI:10.1055/s-2003-41470

Reference yield: 92.0%

(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) → (R)-4-fluorophenylalanine (18125-46-7)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1055/s-2003-41470

upstream raw materials:

((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

Downstream raw materials:

(R)-4-fluorophenylalanine

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