[(3R,3aS)-7-bromo-8-fluoro-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl 3-nitrobenzene-1-sulfonate

Base Information

Chemical Name:[(3R,3aS)-7-bromo-8-fluoro-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl 3-nitrobenzene-1-sulfonate
CAS No.:1341209-34-4
Molecular Formula:C₁₇H₁₂BrFN₂O₈S
Molecular Weight:503.259
Hs Code.:

Synonyms:[(3R,3aS)-7-bromo-8-fluoro-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl 3-nitrobenzene-1-sulfonate

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Chemical Property of [(3R,3aS)-7-bromo-8-fluoro-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl 3-nitrobenzene-1-sulfonate

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Technology Process of [(3R,3aS)-7-bromo-8-fluoro-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl 3-nitrobenzene-1-sulfonate

There total 8 articles about [(3R,3aS)-7-bromo-8-fluoro-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl 3-nitrobenzene-1-sulfonate 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: 87.3%

: 1341209-32-2
(3R,3aS)-7-bromo-8-fluoro-3-(hydroxymethyl)-3a,4-dihydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-1(3H)-one

: 121-51-7
3-nitrobenzenesulphonyl chloride

: 1341209-34-4
[(3R,3aS)-7-bromo-8-fluoro-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl 3-nitrobenzene-1-sulfonate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/jm200614t

Reference yield:

: 1341209-27-5
(Z)-4-(5-bromo-4-fluoro-2-nitrophenoxy)but-2-en-1-ol

: 1341209-34-4
[(3R,3aS)-7-bromo-8-fluoro-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl 3-nitrobenzene-1-sulfonate

Guidance literature:: Multi-step reaction with 7 steps

1: ammonium chloride; zinc / methanol / 24 h / 20 °C

2: sodium hydrogencarbonate / water; acetone / 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

With 1H-imidazole; tert.-butylhydroperoxide; dmap; n-butyllithium; titanium acetate; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; ammonium chloride; triethylamine; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 3: Sharpless epoxidation;
DOI:10.1021/jm200614t

Reference yield:

: 167415-27-2
1-bromo-2,5-difluoro-4-nitrobenzene

: 1341209-34-4
[(3R,3aS)-7-bromo-8-fluoro-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl 3-nitrobenzene-1-sulfonate

Guidance literature:: Multi-step reaction with 8 steps

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

1.2: 1 h / 20 °C

2.1: ammonium chloride; zinc / methanol / 24 h / 20 °C

3.1: sodium hydrogencarbonate / water; acetone / 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

With 1H-imidazole; tert.-butylhydroperoxide; dmap; n-butyllithium; titanium acetate; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; ammonium chloride; triethylamine; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; mineral oil; 4.1: Sharpless epoxidation;
DOI:10.1021/jm200614t