tert-butyl (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(tert-butoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetate

Base Information

• Chemical Name: tert-butyl (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(tert-butoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetate
• CAS No.: 215719-45-2
• Molecular Formula: C₂₅H₃₄N₄O₇
• Molecular Weight: 502.568
• Mol file: 215719-45-2.mol

Synonyms:tert-butyl (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(tert-butoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetate

Chemical Property of tert-butyl (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(tert-butoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(tert-butoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetate

There total 15 articles about tert-butyl (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(tert-butoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetate 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: 100.0%

methyl {N2-[(benzyloxy)carbonyl]-O4-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-43-0) → tert-butyl (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(tert-butoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetate (215719-45-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1039/a804412k

Reference yield:

methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-42-9) → tert-butyl (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(tert-butoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetate (215719-45-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / HATU; 1-hydroxy-7-aza-1H-benzotriazole; i-Pr₂EtN / CH₂Cl₂ / 24 h / 20 °C

2: 100 percent / H₂ / Pd/C / dimethylformamide / 120 h

With 1-hydroxy-7-aza-benzotriazole; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Cyclization;

DOI:10.1002/(SICI)1522-2675(20000216)83:2<444::AID-HLCA444>3.0.CO;2-R

Reference yield:

methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-37-2) → tert-butyl (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(tert-butoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetate (215719-45-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / H₂ / Pd/C / dimethylformamide / 36 h

2: 80 percent / HATU; 1-hydroxy-7-aza-1H-benzotriazole; i-Pr₂EtN / CH₂Cl₂ / 24 h / 20 °C

3: 100 percent / H₂ / Pd/C / dimethylformamide / 120 h

With 1-hydroxy-7-aza-benzotriazole; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide; 1: Catalytic hydrogenation / 2: Acylation / 3: Cyclization;

DOI:10.1002/(SICI)1522-2675(20000216)83:2<444::AID-HLCA444>3.0.CO;2-R

upstream raw materials:

methyl {N²-[(benzyloxy)carbonyl]-O⁴-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate

(1S,4R,5R)-4-Benzoylamino-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Downstream raw materials:

((3S,7R,8R,8aS)-8-Amino-7-benzoylamino-1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazin-3-yl)-acetic acid