tert-butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyrimidinyl]-1-piperazinecarboxylate

Base Information

• Chemical Name: tert-butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyrimidinyl]-1-piperazinecarboxylate
• CAS No.: 1188335-18-3
• Molecular Formula: C₂₅H₃₁FN₆O₅
• Molecular Weight: 514.557
• Mol file: 1188335-18-3.mol

Synonyms:tert-butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyrimidinyl]-1-piperazinecarboxylate

Chemical Property of tert-butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyrimidinyl]-1-piperazinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyrimidinyl]-1-piperazinecarboxylate

There total 1 articles about tert-butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyrimidinyl]-1-piperazinecarboxylate 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: 81.0%

(S)‐N‐((3‐(3‐fluoro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)‐2‐oxooxazolidin‐5‐yl)methyl)acetamide (504437-66-5) + tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (374930-88-8) → tert-butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyrimidinyl]-1-piperazinecarboxylate (1188335-18-3)

Guidance literature:

With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; toluene; for 5h; Inert atmosphere; Reflux;

Reference yield: 94.0%

tert-butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyrimidinyl]-1-piperazinecarboxylate (1188335-18-3) → N-[((5S)-3-{3-fluoro-4-[2-(1-piperazinyl)-5-pyrimidinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide (380382-62-7)

Guidance literature:

tert-butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyrimidinyl]-1-piperazinecarboxylate; With trifluoroacetic acid; In dichloromethane; for 1.5h;

With sodium hydroxide; In water; ethyl acetate;

Reference yield:

tert-butyl 4-[5-(4-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-2-pyrimidinyl]-1-piperazinecarboxylate (1188335-18-3) → N-({(5S)-3-[3-fluoro-4-(2-{4-[(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b][1,3]oxazol-2-yl)methyl]-1-piperazinyl}-5-pyrimidinyl)-phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (1188918-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 1.5 h

2.1: isopropyl alcohol / 16 h / Reflux

2.2: 5 - 20 °C

With trifluoroacetic acid; In dichloromethane; isopropyl alcohol;

upstream raw materials:

(S)‐N‐((3‐(3‐fluoro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)‐2‐oxooxazolidin‐5‐yl)methyl)acetamide

tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate

Downstream raw materials:

N-[((5S)-3-{3-fluoro-4-[2-(1-piperazinyl)-5-pyrimidinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide

N-({(5S)-3-[3-fluoro-4-(2-{4-[(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b][1,3]oxazol-2-yl)methyl]-1-piperazinyl}-5-pyrimidinyl)-phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide

Refernces