tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate

Base Information

Chemical Name:tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate
CAS No.:1384462-00-3
Molecular Formula:C₁₈H₂₀BrF₃N₂O₃S
Molecular Weight:481.334
Hs Code.:

Synonyms:tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate

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Chemical Property of tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate

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Technology Process of tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate

There total 12 articles about tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate 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:

: 24424-99-5
di-tert-butyl dicarbonate

: 1384461-99-7
(4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine

: 1384462-00-3
tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate

Guidance literature:: With triethylamine; In tetrahydrofuran; at 100 ℃; for 1h;

Reference yield:

: 38361-37-4
1-chloro-2,6-difluorobenzene

: 1384462-00-3
tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -75 °C / Inert atmosphere

1.2: 1 h / -78 °C

2.1: zinc; acetic acid / 20 °C

3.1: ammonium formate / palladium 10% on activated carbon / methanol / 20 °C / Inert atmosphere

4.1: dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: trifluoromethylsulfonic anhydride / pyridine / 2.17 h / -20 - 20 °C / Inert atmosphere

6.1: formic acid / water / 2.67 h / 20 °C

6.2: 0.5 h / 20 °C

7.1: Nonafluorobutanesulfonyl fluoride; triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 2.17 h / 0 - 20 °C / Inert atmosphere; Cooling with ice

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 20 - 65 °C / Inert atmosphere

9.1: N-Bromosuccinimide; sulfuric acid / sulfolane; trifluoroacetic acid / 0.75 h / 60 °C

10.1: triethylamine / tetrahydrofuran / 1 h / 100 °C

With 2,2,6,6-tetramethyl-piperidine; N-Bromosuccinimide; n-butyllithium; formic acid; Nonafluorobutanesulfonyl fluoride; trifluoromethylsulfonic anhydride; sulfuric acid; ammonium formate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride); triethylamine; zinc; palladium 10% on activated carbon; In tetrahydrofuran; pyridine; sulfolane; methanol; hexane; dichloromethane; water; trifluoroacetic acid;

Reference yield:

: 1174321-93-7
(3aR,4S)-4-((trityloxy)methyl)-3,3a,4,6-tetrahydrofuro[3,4-c]isoxazole

: 1384462-00-3
tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -75 °C / Inert atmosphere

1.2: 1 h / -78 °C

2.1: zinc; acetic acid / 20 °C

3.1: ammonium formate / palladium 10% on activated carbon / methanol / 20 °C / Inert atmosphere

4.1: dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: trifluoromethylsulfonic anhydride / pyridine / 2.17 h / -20 - 20 °C / Inert atmosphere

6.1: formic acid / water / 2.67 h / 20 °C

6.2: 0.5 h / 20 °C

7.1: Nonafluorobutanesulfonyl fluoride; triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 2.17 h / 0 - 20 °C / Inert atmosphere; Cooling with ice

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 20 - 65 °C / Inert atmosphere

9.1: N-Bromosuccinimide; sulfuric acid / sulfolane; trifluoroacetic acid / 0.75 h / 60 °C

10.1: triethylamine / tetrahydrofuran / 1 h / 100 °C

With 2,2,6,6-tetramethyl-piperidine; N-Bromosuccinimide; n-butyllithium; formic acid; Nonafluorobutanesulfonyl fluoride; trifluoromethylsulfonic anhydride; sulfuric acid; ammonium formate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride); triethylamine; zinc; palladium 10% on activated carbon; In tetrahydrofuran; pyridine; sulfolane; methanol; hexane; dichloromethane; water; trifluoroacetic acid;