(2S,3R)-3-[N-(t-butoxycarbonyl)-2-ethyl-3-(4-bromophenyl)aziridine-2-carbonyl]-oxazolidin-2-one

Base Information

Chemical Name:(2S,3R)-3-[N-(t-butoxycarbonyl)-2-ethyl-3-(4-bromophenyl)aziridine-2-carbonyl]-oxazolidin-2-one
CAS No.:1309658-21-6
Molecular Formula:C₁₉H₂₃BrN₂O₅
Molecular Weight:439.306
Hs Code.:

Synonyms:(2S,3R)-3-[N-(t-butoxycarbonyl)-2-ethyl-3-(4-bromophenyl)aziridine-2-carbonyl]-oxazolidin-2-one

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Chemical Property of (2S,3R)-3-[N-(t-butoxycarbonyl)-2-ethyl-3-(4-bromophenyl)aziridine-2-carbonyl]-oxazolidin-2-one

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Technology Process of (2S,3R)-3-[N-(t-butoxycarbonyl)-2-ethyl-3-(4-bromophenyl)aziridine-2-carbonyl]-oxazolidin-2-one

There total 5 articles about (2S,3R)-3-[N-(t-butoxycarbonyl)-2-ethyl-3-(4-bromophenyl)aziridine-2-carbonyl]-oxazolidin-2-one 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: 68.0%

: 479423-43-3
tert-butyl 4-bromobenzylidenecarbamate

: 1309658-12-5
3-(2-diazobutanoyl)oxazolidin-2-one

: 1309658-21-6
(2S,3R)-3-[N-(t-butoxycarbonyl)-2-ethyl-3-(4-bromophenyl)aziridine-2-carbonyl]-oxazolidin-2-one

Guidance literature:: With (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; C₃₈H₂₅BO₃; C₄₄H₃₀B₂O₅; In dichloromethane; at -78 ℃; for 8h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ja203754p

Reference yield:

: 60420-28-2
3-butyryloxazolidin-2-one

: 1309658-21-6
(2S,3R)-3-[N-(t-butoxycarbonyl)-2-ethyl-3-(4-bromophenyl)aziridine-2-carbonyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 4.5 h / -78 °C / Inert atmosphere

2.1: (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; C₃₈H₂₅BO₃; C₄₄H₃₀B₂O₅ / dichloromethane / 8 h / -78 °C / Inert atmosphere

With (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; C₃₈H₂₅BO₃; C₄₄H₃₀B₂O₅; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja203754p

Reference yield:

: 4248-19-5
tert-butyl carbazate

: 1309658-21-6
(2S,3R)-3-[N-(t-butoxycarbonyl)-2-ethyl-3-(4-bromophenyl)aziridine-2-carbonyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: formic acid / methanol; water / 72 h / 20 °C

2: potassium carbonate; sodium sulfate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux

3: (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; C₃₈H₂₅BO₃; C₄₄H₃₀B₂O₅ / dichloromethane / 8 h / -78 °C / Inert atmosphere

With formic acid; (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; C₃₈H₂₅BO₃; C₄₄H₃₀B₂O₅; potassium carbonate; sodium sulfate; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/ja203754p