N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide

Base Information

• Chemical Name: N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide
• CAS No.: 1174322-00-9
• Molecular Formula: C₂₀H₁₈F₂N₂O₂S
• Molecular Weight: 388.438
• Mol file: 1174322-00-9.mol

Synonyms:N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide

Chemical Property of N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide

There total 5 articles about N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide 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:

(S)-2-((1-fluorobut-3-en-2-yl)oxy)-N-methoxy-N-methylacetamide (1391001-88-9) → N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide (1174322-00-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / -78 - -60 °C / Inert atmosphere

1.2: -78 - -60 °C

2.1: hydroxylamine hydrochloride; sodium acetate / methanol / 1.5 h / 50 °C

3.1: hydroquinone / xylene / 5 h / Reflux

4.1: zinc; acetic acid / 0 - 20 °C

5.1: dichloromethane / 18 h / 0 - 20 °C

6.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 2.08 h / 0 - 18 °C

With pyridine; n-butyllithium; trifluoromethylsulfonic anhydride; hydroxylamine hydrochloride; sodium acetate; acetic acid; hydroquinone; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; xylene;

Reference yield:

((2S,3R,4S)-4-amino-2-(fluoromethyl)-4-(2-fluorophenyl)tetrahydrofuran-3-yl)methanol (1391001-92-5) → N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide (1174322-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 18 h / 0 - 20 °C

2: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 2.08 h / 0 - 18 °C

With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane;

Reference yield:

(S)-2-((1-fluorobut-3-en-2-yl)oxy)-1-(2-fluorophenyl)ethanone oxime (1391001-90-3) → N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide (1174322-00-9)

Guidance literature:

Multi-step reaction with 4 steps

1: hydroquinone / xylene / 5 h / Reflux

2: zinc; acetic acid / 0 - 20 °C

3: dichloromethane / 18 h / 0 - 20 °C

4: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 2.08 h / 0 - 18 °C

With pyridine; trifluoromethylsulfonic anhydride; acetic acid; hydroquinone; zinc; In dichloromethane; xylene;

upstream raw materials:

(S)-2-((1-fluorobut-3-en-2-yl)oxy)-N-methoxy-N-methylacetamide

(S)-2-((1-fluorobut-3-en-2-yl)oxy)-1-(2-fluorophenyl)ethanone

(S)-2-((1-fluorobut-3-en-2-yl)oxy)-1-(2-fluorophenyl)ethanone oxime

((2S,3R,4S)-4-amino-2-(fluoromethyl)-4-(2-fluorophenyl)tetrahydrofuran-3-yl)methanol

Downstream raw materials:

(4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine

tert-butyl ((4aS,5S,7aS)-7a-(2-fluoro-5-(5-methoxypyrazine-2-carboxamido)phenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate

(4aS,5S,7aS)-7a-(2-fluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine

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