tert-butyl(4aR,7aR)-2-benzamido-7a-(isothiazol-5-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate

Base Information

• Chemical Name: tert-butyl(4aR,7aR)-2-benzamido-7a-(isothiazol-5-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate
• CAS No.: 1463485-01-9
• Molecular Formula: C₂₁H₂₄N₄O₃S₂
• Molecular Weight: 444.579
• Mol file: 1463485-01-9.mol

Synonyms:tert-butyl (4aR,7aR)-2-benzamido-7a-(isothiazol-5-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Chemical Property of tert-butyl(4aR,7aR)-2-benzamido-7a-(isothiazol-5-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 tert-butyl(4aR,7aR)-2-benzamido-7a-(isothiazol-5-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate

There total 16 articles about tert-butyl(4aR,7aR)-2-benzamido-7a-(isothiazol-5-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%

tert-butyl (3R,4R)-3-amino-4-(hydroxymethyl)-3-isothiazol-5-yl-pyrrolidine-1-carboxylate (1463486-06-7) + Benzoyl isothiocyanate (532-55-8) → tert-butyl (4aR,7aR)-2-benzamido-7a-(isothiazol-5-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (1463485-01-9)

Guidance literature:

tert-butyl (3R,4R)-3-amino-4-(hydroxymethyl)-3-isothiazol-5-yl-pyrrolidine-1-carboxylate; Benzoyl isothiocyanate; In tetrahydrofuran; at 0 - 20 ℃; for 1.5h;

With 1,1'-carbonyldiimidazole; at 20 - 65 ℃; for 14h;

Reference yield: 34.0%

tert-butyl (±)-2-benzamido-7a-(isothiazol-5-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate → tert-butyl (4aR,7aR)-2-benzamido-7a-(isothiazol-5-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (1463485-01-9) + tert-butyl (4aS,7aS)-2-benzamido-7a-(isothiazol-5-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Guidance literature:

With chiral SFC (Column: Chiralpak IC 50×150; Resolution of racemate;

Reference yield:

tert-butyl 6a-isothiazol-5-yl-1-[(4-methoxyphenyl)methyl]-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate (1463484-92-5) → tert-butyl (4aR,7aR)-2-benzamido-7a-(isothiazol-5-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (1463485-01-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetyl chloride; isopropyl alcohol / 1 h / 45 °C

1.2: 1 h / 70 °C

1.3: 1 h / 10 - 25 °C

2.1: zinc; acetic acid / 8 h / 40 °C

3.1: isopropyl alcohol / 0.5 h / 70 °C

4.1: hydrogenchloride / water; ethyl acetate / 0.25 h / 20 °C / pH 2

5.1: tetrahydrofuran / 1.5 h / 0 - 20 °C

5.2: 14 h / 20 - 65 °C

With hydrogenchloride; acetic acid; acetyl chloride; isopropyl alcohol; zinc; In tetrahydrofuran; water; ethyl acetate; isopropyl alcohol;

upstream raw materials:

tert-butyl (3R,4R)-3-amino-4-(hydroxymethyl)-3-isothiazol-5-yl-pyrrolidine-1-carboxylate

Benzoyl isothiocyanate

tert-butyl 6a-isothiazol-5-yl-1-[(4-methoxyphenyl)methyl]-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate

tert-butyl 6a-isothiazol-5-yl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate

Downstream raw materials:

N-[(4aR,7aR)-7a-isothiazol-5-yl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide hydrochloride

N-[(4aR,7aR)-6-[5-fluoro-4-(1-hydroxy-1-methyl-ethyl)-6-methyl-pyrimidin-2-yl]-7a-isothiazol-5-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide