PHENYL-ACETIC ACID 2,5-DIOXO-PYRROLIDIN-1-YL ESTER synthesis
- Product Name:PHENYL-ACETIC ACID 2,5-DIOXO-PYRROLIDIN-1-YL ESTER
- CAS Number:23776-85-4
- Molecular formula:C12H11NO4
- Molecular Weight:233.22
Yield:23776-85-4 96%
Reaction Conditions:
with dicyclohexyl-carbodiimide at 0 - 20; for 8.5 h;
Steps:
4.2.1. General Synthetic Method for the Preparation of N-Hydroxysuccinimide Esters of Carboxylic and Amino Acids
General procedure: To a well-stirred solution of 17 mmol of acid in 50 mlTHF (or ethylacetate) was added 18 mmol HOSu, then thesolution was cooled to 0°C, and 18 mmol of DCCwas added, ensuring that the temperature did not exceed0 - + 5°C. Stirring continued for 30 min at + 5 °C and then 8h at room temperature. DCU was filtered off, the solutionwas evaporated. The resulting oil was triturated with hexaneto remove the excess of DCC, hexane was decanted. The oilwas dissolved in 30 ml of dichloromethane. The solution waskept at cool temperature (+5 - +8°C) for 24 hours, the reprecipitateof DCU was filtered off, the solution was washedwith 5% NaHCO3. Organic layer was dried using anhydrousMgSO4 or CaCl2, filtered, the solvent was evaporated. Productwas obtained as crystals or viscous yellow oil.
References:
Deeva, Olga A.;Dyabina, Alina S.;Gudasheva, Tatiana A.;Mokrov, Grigory V.;Seredenin, Sergey B.;Yarkova, Milada A. [Medicinal Chemistry,2019,vol. 15,# 4,p. 383 - 399]
