[(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidin-5-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Base Information

• Chemical Name: [(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidin-5-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone
• CAS No.: 162189-18-6
• Molecular Formula: C₃₄H₃₆N₂O₆S
• Molecular Weight: 600.736

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

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

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

There total 5 articles about [(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidin-5-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-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: 94.0%

N-[(1S,2R)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-(4-methoxy-benzyloxy)-3-oxo-1-phenyl-propyl]-benzamide (162189-17-5) → [(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidin-5-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (162189-18-6)

Guidance literature:

With 3 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; at 20 ℃; for 51h;

DOI:10.1039/c39940002591

Reference yield:

N-benzylidenebenzamide (10374-29-5) → [(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidin-5-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (162189-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / LiN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

2: 94 percent / DDQ, molecular sieves 3 Angstroem / acetonitrile / 51 h / 20 °C

With 3 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile;

DOI:10.1039/c39940002591

Reference yield:

(+)-camphorsultam (108448-77-7,124224-04-0) → [(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidin-5-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (162189-18-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / NaH / toluene / 3 h / 20 °C

2: 68 percent / LiN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

3: 94 percent / DDQ, molecular sieves 3 Angstroem / acetonitrile / 51 h / 20 °C

With 3 A molecular sieve; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; toluene; acetonitrile;

DOI:10.1039/c39940002591

upstream raw materials:

N-[(1S,2R)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-methoxy-benzyloxy)-3-oxo-1-phenyl-propyl]-benzamide

N-benzylidenebenzamide

(+)-camphorsultam

N-<<(p-Methoxybenzyl)oxy>acetyl>-2,10-camphorsultam

Downstream raw materials:

(2R,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

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