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

Base Information

• Chemical Name: Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester
• CAS No.: 392660-03-6
• Molecular Formula: C₂₂H₃₀FN₃O₇S
• Molecular Weight: 499.561

Synonyms:

Chemical Property of Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester

There total 7 articles about Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester 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:

[(1S,5R,6S)-3-(2-Fluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-methyl-carbamic acid tert-butyl ester (392659-99-3) → Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester (392660-03-6)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: NaHCO₃ / tetrahydrofuran

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

3.2: tetrahydrofuran

4.1: TEA / CH₂Cl₂ / 0 - 20 °C

With n-butyllithium; TEA; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.bmcl.2005.06.063

Reference yield:

[(1α,5α,6α)-3-(2-fluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester (392659-98-2) → Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester (392660-03-6)

Guidance literature:

Multi-step reaction with 5 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

With n-butyllithium; TEA; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.bmcl.2005.06.063

Reference yield:

3,4-difluoronitrobenzene (369-34-6) → Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester (392660-03-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N-ethyldiisopropylamine / acetonitrile / 80 °C

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

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

4.1: NaHCO₃ / tetrahydrofuran

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

5.2: tetrahydrofuran

6.1: TEA / CH₂Cl₂ / 0 - 20 °C

With n-butyllithium; TEA; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.bmcl.2005.06.063

upstream raw materials:

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

methanesulfonyl chloride

[(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

Downstream 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-[4-((S)-5-Aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester

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

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

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