Technology Process of N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(oxiran-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide
There total 10 articles about N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(oxiran-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide which
guide to synthetic route it.
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synthetic route:
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N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-formyl-4,4-a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide
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1616505-12-4
N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(oxiran-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide
- Guidance literature:
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trimethylsulfoxonium iodide;
With
sodium hydride;
In
dimethyl sulfoxide; mineral oil;
for 0.5h;
Cooling with ice;
N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-formyl-4,4-a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide;
In
dimethyl sulfoxide; mineral oil;
at 20 ℃;
for 2h;
Cooling with ice;
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1616505-12-4
N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(oxiran-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: sodium hypochlorite / water; dichloromethane / 0 - 15 °C
2.1: boron trifluoride diethyl etherate / toluene; di-isopropyl ether / 0.5 h / -76 °C
2.2: 1.5 h / -76 - -71 °C
3.1: acetic acid; zinc / 16 h / 20 - 40 °C
4.1: dichloromethane / 18 h / 20 °C
5.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 3 h / -60 - -5 °C
6.1: boron trichloride / dichloromethane; n-heptane / 4.25 h / 0 - 20 °C
7.1: triethylamine; dimethyl sulfoxide; sulfur trioxide pyridine complex / dichloromethane / 6.5 h / 20 °C
8.1: sodium hydride / mineral oil; dimethyl sulfoxide / 0.5 h / Cooling with ice
8.2: 2 h / 20 °C / Cooling with ice
With
pyridine; sodium hypochlorite; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; sulfur trioxide pyridine complex; boron trichloride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; zinc;
In
n-heptane; dichloromethane; di-isopropyl ether; water; dimethyl sulfoxide; toluene; mineral oil;
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1616505-12-4
N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(oxiran-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide
- Guidance literature:
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Multi-step reaction with 7 steps
1.1: boron trifluoride diethyl etherate / toluene; di-isopropyl ether / 0.5 h / -76 °C
1.2: 1.5 h / -76 - -71 °C
2.1: acetic acid; zinc / 16 h / 20 - 40 °C
3.1: dichloromethane / 18 h / 20 °C
4.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 3 h / -60 - -5 °C
5.1: boron trichloride / dichloromethane; n-heptane / 4.25 h / 0 - 20 °C
6.1: triethylamine; dimethyl sulfoxide; sulfur trioxide pyridine complex / dichloromethane / 6.5 h / 20 °C
7.1: sodium hydride / mineral oil; dimethyl sulfoxide / 0.5 h / Cooling with ice
7.2: 2 h / 20 °C / Cooling with ice
With
pyridine; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; sulfur trioxide pyridine complex; boron trichloride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; zinc;
In
n-heptane; dichloromethane; di-isopropyl ether; dimethyl sulfoxide; toluene; mineral oil;