benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-bromothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate

Base Information

• Chemical Name: benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-bromothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate
• CAS No.: 1463485-06-4
• Molecular Formula: C₂₅H₂₂BrN₃O₃S₂
• Molecular Weight: 556.504
• Mol file: 1463485-06-4.mol

Synonyms:benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-bromothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate

Chemical Property of benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-bromothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-bromothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate

There total 10 articles about benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-bromothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate 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:

benzyl 3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate (1463484-39-0) → benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-bromothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate (1463485-06-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.17 h / Inert atmosphere

1.2: 1 h / -78 °C

2.1: zinc; acetic acid / 2 h / 20 °C / Inert atmosphere

3.1: tetrahydrofuran / 2 h / 0 °C

4.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0 - 20 °C

5.1: SFC (Column: Chiralpak IC / methanol / Resolution of racemate

6.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.83 h / 20 °C / Inert atmosphere

With N-Bromosuccinimide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; boron trifluoride diethyl etherate; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

benzyl rel-(4aR,7aR)-2-benzamido-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate → benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-bromothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate (1463485-06-4)

Guidance literature:

Multi-step reaction with 2 steps

1: SFC (Column: Chiralpak IC / methanol / Resolution of racemate

2: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.83 h / 20 °C / Inert atmosphere

With N-Bromosuccinimide; In methanol; N,N-dimethyl-formamide;

Reference yield:

benzyl 6a-(2-thienyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate (1463484-43-6) → benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-bromothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate (1463485-06-4)

Guidance literature:

Multi-step reaction with 5 steps

1: zinc; acetic acid / 2 h / 20 °C / Inert atmosphere

2: tetrahydrofuran / 2 h / 0 °C

3: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0 - 20 °C

4: SFC (Column: Chiralpak IC / methanol / Resolution of racemate

5: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.83 h / 20 °C / Inert atmosphere

With N-Bromosuccinimide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

benzyl 3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate

benzyl 6a-(2-thienyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate

benzyl 3-amino-4-(hydroxymethyl)-3-(2-thienyl)pyrrolidine-1-carboxylate

benzyl 3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-(2-thienyl)pyrrolidine-1-carboxylate

Downstream raw materials:

N-[(4aR,7aR)-7a-(5-cyanothiophen-2-yl)-4,4a,5,6,7,7a-hexahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

N-{(4aR,7aR)-7a-(5-cyanothiophen-2-yl)-6-[5-fluoro-4-(2-hydroxypropan-2-yl)pyrimidin-2-yl]-4,4a,5,6,7,7a-hexahydropyrrolo[3,4-d][1,3]thiazin-2-yl}benzamide

benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-cyanothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate