Ketorolac methyl ester

Base Information

• Chemical Name: Ketorolac methyl ester
• CAS No.: 80965-09-9
• Molecular Formula: C16H15NO3
• Molecular Weight: 269.3
• UNII: 884M437C95
• Wikidata: Q27269885
• Mol file: 80965-09-9.mol

Synonyms:Ketorolac methyl ester;80965-09-9;Methyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylate;(+/-)-Ketorolac methyl ester;Ketorolac methyl ester, (RS)-;1H-Pyrrolizine-1-carboxylic acid, 5-benzoyl-2,3-dihydro-, methyl ester;UNII-884M437C95;Ketorolac trometamol impurity H [EP];Methyl (1RS)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylate;884M437C95;Methyl (1RS)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylate (Ketorolac Methyl Ester);Ketorolac Trometamol Imp. H (EP);5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid methyl ester;Ketorolac Trometamol Impurity H;Ketorolac Impurity H;SCHEMBL9387346;GREBGQSAVFHEAD-UHFFFAOYSA-N;AKOS040708071;KETOROLAC TROMETAMOL IMPURITY H [EP IMPURITY];Q27269885;Methyl5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylate;methyl 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate;5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid methyl ester

Chemical Property of Ketorolac methyl ester

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 269.10519334
• Heavy Atom Count: 20
• Complexity: 389

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCN2C1=CC=C2C(=O)C3=CC=CC=C3

Technology Process of Ketorolac methyl ester

There total 10 articles about Ketorolac methyl 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: 73.0%

methanol (67-56-1) + Ketorolac (74103-06-3) → 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid methyl ester (80965-09-9)

Guidance literature:

With thionyl chloride; for 14h; Inert atmosphere; Reflux;

DOI:10.1039/c3md00258f

Reference yield: 61.0%

4-(2-benzoylpyrrol-1-yl)-2-iodobutyric acid methyl ester (189696-36-4) → 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid methyl ester (80965-09-9)

Guidance literature:

With triethyl borane; In hexane; dimethyl sulfoxide;

Reference yield:

ketorolac tromethamine → (1,2-dihydroxy-2,3-dihydro-1H-pyrrolizin-5-yl)(phenyl)methanone + 5-formyl-3H-pyrrolizine-1-carboxylic acid + 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid methyl ester (80965-09-9) + benzaldehyde (100-52-7)

Guidance literature:

With hydrogenchloride; In water; at 40 ℃; for 360h; Photolysis;

DOI:10.1002/jms.3351

upstream raw materials:

2-[2-(2-Benzoyl-5-methanesulfonyl-pyrrol-1-yl)-ethyl]-malonic acid dimethyl ester

2-(methylthio)-5-benzoylpyrrole

2-(methylsulfonyl)-5-benzoylpyrrole

5-[2-(2-Benzoyl-5-methylsulfanyl-pyrrol-1-yl)-ethyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione

Downstream raw materials:

C₁₆H₁₃N₃O₂S

3-[2-{5-(5-benzoyl-2,3-dihydro-1H-pyrrolizin-1-yl)-1,3,4-oxadiazol-2-ylthio}acetyl]-2H-chromen-2-one

R-(+)-ketorolac

(-)-(S)-ketorolac methyl ester

Refernces

• 1、 Juaristi, Eusebio,Pérez-Venegas, Mario,Rodríguez-Trevi?o, Agustín Mario. "Dual Mechanoenzymatic Kinetic Resolution of (±)-Ketorolac". . . Retrieved 2020/02/15.
• 2、 Ingale, Nista,Maddi, Veeresh,Palkar, Mahesh,Ronad, Pradeepkumar,Mamledesai, Shivalingrao,Vishwanathswamy,Satyanarayana, Darbhamulla. "Synthesis and evaluation of anti-inflammatory and analgesic activity of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-ones". experimental part. p. 16 - 36. Retrieved 2012/06/04.