3-Oxo-cyclobutanecarboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester

Base Information

• Chemical Name: 3-Oxo-cyclobutanecarboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester
• CAS No.: 939412-81-4
• Molecular Formula: C9H9NO5
• Molecular Weight: 211.174
• Mol file: 939412-81-4.mol

Synonyms:3-OXO-CYCLOBUTANECARBOXYLIC ACID 2,5-DIOXO-PYRROLIDIN-1-YL ESTE;

Chemical Property of 3-Oxo-cyclobutanecarboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester

Chemical Property:

• Boiling Point: 365.9±52.0 °C (760 mmHg)
• PSA: 80.75000
• Density: 1.48±0.1 g/cm3(20 °C , 760mmHg)
• LogP: -0.48940

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,5-Dioxopyrrolidin-1-yl 3-oxocyclobutanecarboxylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Oxo-cyclobutanecarboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester

There total 2 articles about 3-Oxo-cyclobutanecarboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester 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:

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 3-oxocyclobutanecarboxylic acid (23761-23-1) → 3-oxocyclobutanecarboxylic acid 2,5-dioxopyrrolidin-1-yl ester (939412-81-4) + urea (57-13-6)

Guidance literature:

With dicyclohexyl-carbodiimide; In Isopropyl acetate; at 20 ℃; for 1h;

Reference yield:

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 3-oxocyclobutanecarboxylic acid (23761-23-1) → 3-oxocyclobutanecarboxylic acid 2,5-dioxopyrrolidin-1-yl ester (939412-81-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; at 16 - 45 ℃; for 2h;

Reference yield:

3-oxocyclobutanecarboxylic acid 2,5-dioxopyrrolidin-1-yl ester (939412-81-4) → C29H27FN8O

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hydrogencarbonate / tetrahydrofuran; water / 20 °C

2: trichlorophosphate / N,N-dimethyl-formamide; acetonitrile / 20 °C

3: N-Bromosuccinimide / N,N-dimethyl-formamide

4: ammonia / isopropyl alcohol / 50 °C

5: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C

6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 95 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; ammonia; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; potassium carbonate; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 6: Suzuki coupling;

DOI:10.1021/ml100178g

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

3-oxocyclobutanecarboxylic acid

Downstream raw materials:

3-(8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutanone

N-[(2-chlorophenyl(methyl))]-3-oxocyclobutanecarboxamide

C₂₅H₂₁FN₆O

Refernces

• 1、 -. "Combined treatment with an EGFR kinase inhibitor and an agent that sensitizes tumor cells to the effects of EGFR kinase inhibitors". Page/Page column 57. . Retrieved 2010/11/29.