N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide

Base Information

• Chemical Name: N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide
• CAS No.: 392659-54-0
• Molecular Formula: C₁₈H₂₃FN₄O₃
• Molecular Weight: 362.404
• Mol file: 392659-54-0.mol

Synonyms:N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide

Chemical Property of N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide

There total 12 articles about N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]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:

N-[5(S)-3-[4-[(1α,5α,6α)-6-(N-benzyl-N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]-3-fluorophenyl]-2-oxooxazolidin-5-ylmethyl]acetamide (504435-62-5) → N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide (392659-54-0) + N-[5(S)-3-[3-Fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylethyl]acetamide

Guidance literature:

palladium; In methanol;

Reference yield:

((1S,5R,6S)-3-{4-[(S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-3-aza-bicyclo[3.1.0]hex-6-yl)-methyl-carbamic acid tert-butyl ester (392660-06-9) → N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide (392659-54-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 5 - 20 ℃;

DOI:10.1016/j.bmcl.2005.06.063

Reference yield:

[(1S,5R,6S)-3-(4-Amino-2-fluoro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-methyl-carbamic acid tert-butyl ester (392660-00-3) → N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide (392659-54-0)

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

upstream raw materials:

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

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

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

[(1α,5α,6α)-3-(2-fluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester

Downstream raw materials:

N-[5(S)-3-[4-[(1α,5α,6α)-6-(N-benzyloxyacetyl-N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]-3-fluorophenyl]-2-oxooxazolidin-5-ylmethyl]acetamide