(S)-N-[[3-[3-fluoro-4-[3-(1α,5α,6α)-6-[[N-methyl]aminomethyl]-3-azabicyclo-[3.1.0]hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Base Information

Chemical Name:(S)-N-[[3-[3-fluoro-4-[3-(1α,5α,6α)-6-[[N-methyl]aminomethyl]-3-azabicyclo-[3.1.0]hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
CAS No.:392660-17-2
Molecular Formula:C₁₉H₂₅FN₄O₃
Molecular Weight:376.431
Hs Code.:

Synonyms:(S)-N-[[3-[3-fluoro-4-[3-(1α,5α,6α)-6-[[N-methyl]aminomethyl]-3-azabicyclo-[3.1.0]hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

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Chemical Property of (S)-N-[[3-[3-fluoro-4-[3-(1α,5α,6α)-6-[[N-methyl]aminomethyl]-3-azabicyclo-[3.1.0]hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

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Technology Process of (S)-N-[[3-[3-fluoro-4-[3-(1α,5α,6α)-6-[[N-methyl]aminomethyl]-3-azabicyclo-[3.1.0]hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

There total 11 articles about (S)-N-[[3-[3-fluoro-4-[3-(1α,5α,6α)-6-[[N-methyl]aminomethyl]-3-azabicyclo-[3.1.0]hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 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:

: 392660-16-1
((1S,5R,6R)-3-{4-[(S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-3-aza-bicyclo[3.1.0]hex-6-ylmethyl)-methyl-carbamic acid tert-butyl ester

: 392660-17-2
(S)-N-[[3-[3-fluoro-4-[3-(1α,5α,6α)-6-[[N-methyl]aminomethyl]-3-azabicyclo-[3.1.0]hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 5 - 20 ℃;
DOI:10.1016/j.bmcl.2005.06.063

Reference yield:

: 392660-10-5
[(1S,5R,6R)-3-(4-Amino-2-fluoro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-ylmethyl]-methyl-carbamic acid tert-butyl ester

: 392660-17-2
(S)-N-[[3-[3-fluoro-4-[3-(1α,5α,6α)-6-[[N-methyl]aminomethyl]-3-azabicyclo-[3.1.0]hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaHCO₃ / tetrahydrofuran

2.1: n-BuLi / tetrahydrofuran / 1.5 h / -78 °C

2.2: tetrahydrofuran

3.1: TEA / CH₂Cl₂ / 0 - 20 °C

4.1: NaN₃ / dimethylformamide / 80 °C

5.1: H₂ / Pd/C / methanol / 20 °C / 2844.31 Torr

6.1: TEA / CH₂Cl₂ / 0 - 20 °C

7.1: TFA / CH₂Cl₂ / 5 - 20 °C

With n-butyllithium; sodium azide; TEA; hydrogen; sodium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2005.06.063

Reference yield:

: 392660-08-1
[(1R,5S,6S)-3-(2-Fluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-ylmethyl]-carbamic acid tert-butyl ester

: 392660-17-2
(S)-N-[[3-[3-fluoro-4-[3-(1α,5α,6α)-6-[[N-methyl]aminomethyl]-3-azabicyclo-[3.1.0]hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 0 °C

2.1: H₂ / Pd/C / methanol / 20 °C / 2844.31 Torr

3.1: NaHCO₃ / tetrahydrofuran

4.1: n-BuLi / tetrahydrofuran / 1.5 h / -78 °C

4.2: tetrahydrofuran

5.1: TEA / CH₂Cl₂ / 0 - 20 °C

6.1: NaN₃ / dimethylformamide / 80 °C

7.1: H₂ / Pd/C / methanol / 20 °C / 2844.31 Torr

8.1: TEA / CH₂Cl₂ / 0 - 20 °C

9.1: TFA / CH₂Cl₂ / 5 - 20 °C

With n-butyllithium; sodium azide; TEA; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2005.06.063