benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-cyanothiophen-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-cyanothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate
• CAS No.: 1463485-07-5
• Molecular Formula: C₂₆H₂₂N₄O₃S₂
• Molecular Weight: 502.618
• Mol file: 1463485-07-5.mol

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

There total 13 articles about benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-cyanothiophen-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: 74.0%

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) + potassium hexacyanoferrate(III) → benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-cyanothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate (1463485-07-5)

Guidance literature:

With 1-Butylimidazole; copper(l) iodide; In toluene; at 145 ℃; for 18h; Inert atmosphere; Sealed tube;

Reference yield: 74.0%

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) + potassium ferrocyanide → benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-cyanothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate (1463485-07-5)

Guidance literature:

With 1-Butylimidazole; copper(l) iodide; In toluene; at 140 ℃; for 18h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.jmedchem.1c00489

Reference yield:

benzyl 3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate (1463484-39-0) → benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-cyanothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate (1463485-07-5)

Guidance literature:

Multi-step reaction with 7 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

7.1: 1-Butylimidazole; copper(l) iodide / toluene / 18 h / 145 °C / Inert atmosphere; Sealed tube

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

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 (4aR,7aR)-2-benzamido-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-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