2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester

Base Information

• Chemical Name: 2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester
• CAS No.: 186366-83-6
• Molecular Formula: C₂₆H₃₉NO₇
• Molecular Weight: 477.598
• Mol file: 186366-83-6.mol

Synonyms:2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester

Chemical Property of 2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester

There total 15 articles about 2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl 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:

2-[1-{2-[(E)-5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pent-3-enyl]-phenyl}-meth-(E)-ylidene]-malonic acid benzyl ester methyl ester → 2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester (186366-83-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 17h; under 2585.7 Torr;

DOI:10.1021/jm960582o

Reference yield:

diethyl 2-(2-bromobenzyl)propan-1,3-dioate (66192-11-8) → 2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester (186366-83-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 75 percent / aq. KOH / a) reflux, 7 h, b) RT, overnight

2: 81 percent / 5 h / 180 °C

3: 96 percent / borane*THF complex / tetrahydrofuran / 0.5 h / Heating

4: 29 percent / N-iodosuccinimide, Ph₃P / CH₂Cl₂ / Ambient temperature

5: 70 percent / toluene / 17 h / Heating

6: 51 percent / t-BuOK / CH₂Cl₂; tetrahydrofuran / 0.5 h / 0 °C

7: 71 percent / n-BuLi / tetrahydrofuran / 1 h / -78 - 0 °C

8: 66 percent / piperidine, benzoic acid / toluene / 6 h / Heating

9: 1.9 g / H₂ / 10percent Pd/C / ethyl acetate / 17 h / 2585.7 Torr

With piperidine; potassium hydroxide; N-iodo-succinimide; n-butyllithium; borane-THF; potassium tert-butylate; hydrogen; triphenylphosphine; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jm960582o

Reference yield:

3-(2-bromophenyl)propionic acid (15115-58-9) → 2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester (186366-83-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / borane*THF complex / tetrahydrofuran / 0.5 h / Heating

2: 29 percent / N-iodosuccinimide, Ph₃P / CH₂Cl₂ / Ambient temperature

3: 70 percent / toluene / 17 h / Heating

4: 51 percent / t-BuOK / CH₂Cl₂; tetrahydrofuran / 0.5 h / 0 °C

5: 71 percent / n-BuLi / tetrahydrofuran / 1 h / -78 - 0 °C

6: 66 percent / piperidine, benzoic acid / toluene / 6 h / Heating

7: 1.9 g / H₂ / 10percent Pd/C / ethyl acetate / 17 h / 2585.7 Torr

With piperidine; N-iodo-succinimide; n-butyllithium; borane-THF; potassium tert-butylate; hydrogen; triphenylphosphine; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jm960582o

upstream raw materials:

diethyl 2-(2-bromobenzyl)propan-1,3-dioate

3-(2-bromophenyl)propionic acid

3-(2-bromo-phenyl)-propan-1-ol

<(2-bromophenyl)methyl>propanedicarboxylic acid

Downstream raw materials:

2-[2-((S)-6-Amino-7-hydroxy-heptyl)-benzyl]-malonic acid monomethyl ester