Compound TDG7
2-amino-N,N-diethylacetamide
View in PubChem | MDL Molfile | Chemdraw file
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To a stirring solution of Cbz-Gly-OH (1.05 g, 5 mmol), EDC-HCl (1.15 g, 6 mmol), and HNEt2-HCl (657.6 mg, 6 mmol) in DCM (35 mL), was added N,N-Diisopropylethylamine (1.05 mL, 6 mmol) dropwise at 0 oC. The reaction mixture was slowly warmed to room temperature, and stirred for 24 h. Upon completion, the reaction mixture was diluted with DCM, washed with 10 % KHSO4 (aq), sat. NaHCO3 (aq), and brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography to afford Cbz- Gly-NEt2. The product was directly added to a suspension of 10 wt. % Pd/C (266 mg, 0.25 mmol) in MeOH (50 mL) under N2. The reaction vessel was backfilled with H2 for three times, and the reaction was allowed to stir for 3 h at room temperature with H2 balloon. Upon completion, the reaction mixture was filtered through Celite, concentrated in vacuo to afford TDG7 as a highly hygroscopic solid. The spectroscopic data was consistent with reported values (Ribeiro, L. et al. Aminocarbonyloxymethyl Ester Prodrugs of Flufenamic Acid and Diclofenac: Suppressing the Rearrangement Pathway in Aqueous Media. Arch. Pharm. 340, 32-40 (2007)).
