2,5-Dihydro-4-hydroxy-2-oxo-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: 2,5-Dihydro-4-hydroxy-2-oxo-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester
• CAS No.: 182352-48-3
• Molecular Formula: C9H13NO4
• Molecular Weight: 199.207
• Hs Code.: 2933990090
• Mol file: 182352-48-3.mol

Synonyms:FC0539;4-Hydroxy-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester;1-Boc-4-hydroxy-2-oxo-2,5-dihydro-pyrrole;2-oxo-4-pent-4-enyloxy-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester;2,5-Dihydro-4-hydroxy-2-oxo-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester;tert-butyl 4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate;FC0533;tert-butyl 2,5-dihydro-4-hydroxy-2-oxo-1H-pyrrole-1-carboxylate;

Chemical Property of 2,5-Dihydro-4-hydroxy-2-oxo-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 123-127℃
• Boiling Point: 278.455oC at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 122.206oC
• PSA: 66.84000
• Density: 1.313g/cm3
• LogP: 1.14350

Purity/Quality:

98%Min ^*data from raw suppliers

tert-Butyl4-Hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,5-Dihydro-4-hydroxy-2-oxo-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester

There total 5 articles about 2,5-Dihydro-4-hydroxy-2-oxo-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl 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: 99.0%

BOC-glycine (4530-20-5) + cycl-isopropylidene malonate (2033-24-1) → 2-oxo-4-pent-4-enyloxy-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (182352-48-3)

Guidance literature:

BOC-glycine; cycl-isopropylidene malonate; With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃;

In dichloromethane; ethyl acetate; for 0.5h; Reflux;

DOI:10.1021/jo900799y

Reference yield: 78.0%

BOC-glycine (4530-20-5) + cycl-isopropylidene malonate (2033-24-1) + isopropyl chloroformate (108-23-6) → 2-oxo-4-pent-4-enyloxy-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (182352-48-3)

Guidance literature:

DOI:10.1016/j.tetlet.2006.11.156

Reference yield: 61.0%

BOC-glycine (4530-20-5) + isopropyl chloroformate (108-23-6) → 2-oxo-4-pent-4-enyloxy-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (182352-48-3)

Guidance literature:

BOC-glycine; isopropyl chloroformate; With dmap; cycl-isopropylidene malonate; In dichloromethane; toluene; at 0 ℃; for 4h; Inert atmosphere;

With ethyl acetate; for 1h; Reflux;

DOI:10.1021/acs.jmedchem.5b00560

upstream raw materials:

5-(N-tert-butoxycarbonyglycyl)meldrum’s acid

BOC-glycine

cycl-isopropylidene malonate

isopropyl chloroformate

Downstream raw materials:

1-(tert-butoxycarbonyl)-4-hydroxy-3-(4′-methoxyphenyl)-1H-pyrrol-2(5H)-one

4-(4-chlorophenyl)-2-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

tert-butyl 2,5-dihydro-4-(4'-methoxyphenyl)-2-oxo-1H-pyrrole-1-carboxylate

2-oxo-4-phenyl-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Yoon-Miller, Sarah J.P.,Opalka, Suzanne M.,Pelkey, Erin T.. "Short synthesis of 4-aryl-3-pyrrolin-2-ones". . p. 827 - 830. Retrieved 2007.
• 2、 -. "METHODS AND COMPOSITIONS FOR MODULATING SPLICING". Paragraph 0863. . Retrieved 2020/08/22.
• 3、 -. "TYK2 INHIBITORS AND USES THEREOF". Paragraph 001028-001029. . Retrieved 2017/03/21.