N-{[(3S,3aS)-7-(4-acetylphenyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

Base Information

Chemical Name:N-{[(3S,3aS)-7-(4-acetylphenyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide
CAS No.:1341208-58-9
Molecular Formula:C₂₁H₂₀N₂O₅
Molecular Weight:380.4
Hs Code.:

Synonyms:N-{[(3S,3aS)-7-(4-acetylphenyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

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Chemical Property of N-{[(3S,3aS)-7-(4-acetylphenyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

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Technology Process of N-{[(3S,3aS)-7-(4-acetylphenyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

There total 13 articles about N-{[(3S,3aS)-7-(4-acetylphenyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide 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: 41.7%

: 1341208-52-3
N-{[(3S,3aS)-1-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

: 99-90-1
para-bromoacetophenone

: 1341208-58-9
N-{[(3S,3aS)-7-(4-acetylphenyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; at 80 ℃; for 2h;
DOI:10.1021/jm200614t

Reference yield: 41.5%

: 1341208-58-9
N-{[(3S,3aS)-7-(4-acetylphenyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; water; at 80 ℃; for 2h; Inert atmosphere;

Reference yield:

: 321-23-3
4-bromo-2-fluoronitrobenzene

: 1341208-58-9
N-{[(3S,3aS)-7-(4-acetylphenyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

Guidance literature:: Multi-step reaction with 12 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C

1.2: 1 h / 20 °C

2.1: ammonium chloride; zinc / tetrahydrofuran / 20 °C

3.1: sodium hydrogencarbonate / tetrahydrofuran; water / 0 - 20 °C

4.1: tert.-butylhydroperoxide; titanium acetate; diethyl (2R,3R)-tartrate / dichloromethane; toluene / 20 h / -40 °C / Molecular sieve

5.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C

8.1: triethylamine / dichloromethane / 0 - 20 °C

9.1: ammonium hydroxide / isopropyl alcohol; acetonitrile / 24 h / Heating

10.1: triethylamine / dichloromethane / 0.5 h / 0 °C

11.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C

12.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / 1,4-dioxane / 2 h / 80 °C

With 1H-imidazole; tert.-butylhydroperoxide; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; titanium acetate; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; potassium acetate; sodium hydride; sodium hydrogencarbonate; ammonium chloride; caesium carbonate; ammonium hydroxide; triethylamine; zinc; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; mineral oil; 4.1: Sharpless epoxidation / 12.1: Suzuki coupling;
DOI:10.1021/jm200614t