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
Hs Code.:

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

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

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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

: 186366-83-6
2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; for 17h; under 2585.7 Torr;
DOI:10.1021/jm960582o

Reference yield:

: 66192-11-8
diethyl 2-(2-bromobenzyl)propan-1,3-dioate

: 186366-83-6
2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester

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:

: 15115-58-9
3-(2-bromophenyl)propionic acid

: 186366-83-6
2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester

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