N,N-Dimethylglycine → HCID 58109630, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (0.0465 g, 0.0866 mmol), methanesulfonamide (0.0945 g), K3PO4 (0.2753 g), N,N-dimethylglycine (0.0686 g), and CuI (0.0687 g) in DMF (2 mL) was heated at 120° C. for 17 h. The mixture was diluted with EtOAc, filtered, washed with CH2Cl2. After the solvent was evaporated under reduced pressure, the residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ 5 μm 19×50 mm column, 10%→90% CH3CN/H2O, 0.1% CF3COOH over 8 min and then 90% CH3CN/H2O, 0.1% CF3COOH over 2 min, flow rate 20 mL/min) to afford N-(4-((S)-1-((S)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)ethyl)phenyl)methanesulfonamide. LC-MS tR=2.10 min in 3 min chromatography, m/z 551 (MH+), 507.

Provenance & Evidence