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

Base Information

Chemical Name:N-{[(3S,3aS)-1-oxo-7-phenyl-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide
CAS No.:1341208-55-6
Molecular Formula:C₁₉H₁₈N₂O₄
Molecular Weight:338.363
Hs Code.:

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

There total 11 articles about N-{[(3S,3aS)-1-oxo-7-phenyl-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: 80.2%

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

: 98-80-6
phenylboronic acid

: 1341208-55-6
N-{[(3S,3aS)-1-oxo-7-phenyl-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 tetrahydrofuran; for 24h; Reflux;
DOI:10.1021/jm200614t

Reference yield:

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

: 1341208-55-6
N-{[(3S,3aS)-1-oxo-7-phenyl-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

Guidance literature:: Multi-step reaction with 11 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: tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / tetrahydrofuran / 24 h / Reflux

With 1H-imidazole; tert.-butylhydroperoxide; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; titanium acetate; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; ammonium chloride; caesium carbonate; ammonium hydroxide; triethylamine; zinc; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; mineral oil; 4.1: Sharpless epoxidation / 11.1: Suzuki coupling;
DOI:10.1021/jm200614t

Reference yield:

: 911845-37-9
(2Z)-4-(5-bromo-2-nitrophenoxy)but-2-en-1-ol

: 1341208-55-6
N-{[(3S,3aS)-1-oxo-7-phenyl-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

Guidance literature:: Multi-step reaction with 10 steps

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

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

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

4: 1H-imidazole; dmap / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

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

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

7: triethylamine / dichloromethane / 0 - 20 °C

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

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

10: tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / tetrahydrofuran / 24 h / Reflux

With 1H-imidazole; tert.-butylhydroperoxide; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; titanium acetate; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; ammonium chloride; caesium carbonate; ammonium hydroxide; triethylamine; zinc; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 3: Sharpless epoxidation / 10: Suzuki coupling;
DOI:10.1021/jm200614t