(2S,3R)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carbonyl]-oxazolidin-2-one

Base Information

• Chemical Name: (2S,3R)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carbonyl]-oxazolidin-2-one
• CAS No.: 1309658-14-7
• Molecular Formula: C₁₈H₂₂N₂O₅
• Molecular Weight: 346.383

Synonyms:(2S,3R)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carbonyl]-oxazolidin-2-one

Chemical Property of (2S,3R)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carbonyl]-oxazolidin-2-one

Chemical Property:

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Technology Process of (2S,3R)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carbonyl]-oxazolidin-2-one

There total 8 articles about (2S,3R)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-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: 80.0%

3-(2-diazopropanoyl)oxazolidin-2-one (1218811-94-9) + benzaldehyde N-boc imine (150884-50-7) → (2S,3R)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carbonyl]-oxazolidin-2-one (1309658-14-7)

Guidance literature:

With (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; C₃₈H₂₅BO₃; C₄₄H₃₀B₂O₅; In dichloromethane; at -78 ℃; for 4h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja203754p

Reference yield:

3-(2-diazopropanoyl)oxazolidin-2-one (1218811-94-9) + benzaldehyde N-boc imine (150884-50-7) → (2R,3S)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carbonyl]-oxazolidin-2-one (1309658-16-9) + (2S,3R)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carbonyl]-oxazolidin-2-one (1309658-14-7)

Guidance literature:

With (S)-[3,3’-diphenyl-1,1’-binaphthalen-2,2’-yl]-N-triflyl phosphoramide; In dichloromethane; at -78 ℃; for 1h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja203901h

Reference yield:

rac-(2R,3S)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carbonyl]-oxazolidin-2-one → (2R,3S)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carbonyl]-oxazolidin-2-one (1309658-16-9) + (2S,3R)-3-[N-(t-butoxycarbonyl)-2-methyl-3-phenylaziridine-2-carbonyl]-oxazolidin-2-one (1309658-14-7) + C18H24N2O6 + C18H24N2O6 (1310929-29-3)

Guidance literature:

With (S)-[3,3’-diphenyl-1,1’-binaphthalen-2,2’-yl]-N-triflyl phosphoramide; water; In dichloromethane; at -78 ℃; for 2h; optical yield given as %ee; Inert atmosphere; Resolution of racemate;

DOI:10.1021/ja203901h

upstream raw materials:

N-propionyloxazolidin-2-one

3-(2-diazopropanoyl)oxazolidin-2-one

benzaldehyde N-boc imine

tert-butyl carbazate

Downstream raw materials:

C₁₅H₁₉NO₄

C₂₂H₂₆N₂O₃

C₁₆H₂₁NO₄

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