N,N-Dimethylglycine → HCID 131729368, compound

Participants

Reaction Steps

A mixture of (3aR*,7S*,7aS*)-7-(4-amino-3-fluoro-benzyl)-3-(3-tert-butyl-benzyl)-5,5-dioxo-hexahydro-1oxa-5lambda*6*-thia-3-aza-inden-2-one (example 1j), 1.06 g, 2.3 mmol), N-methylmorpholine (0.507 mL, 4.6 mmol), N,N-dimethylglycine (0.356 g, 3.45 mmol) and propylphosphoric acid anhydride (50% in DMF, 2.68 mL, 4.6 mmol) was stirred in DMF (9.2 mL) at 25° C. for 19 h. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 solution, water and brine. The organic layer was dried over Na2SO4, filtered and evaporated to leave the title compound as a colorless, amorphous powder: TLC (toluene-ETA 85:15) Rf=0.36; HPLC RtA=1.84 min; ESIMS [M+H]+=546; 1H NMR (600 MHz, DMSO-d6): δ 9.46 (s, 1H), 7.85 (t, 1H), 7.39 (s, 1H), 7.32 (d, 1H), 7.28 (t, 1H), 7.17-7.11 (m, 2H), 7.0 (d, 1H), 4.42 (d, 1H), 4.23 (d, 1H), 4.16 (t, 1H), 3.74-3.65 (m, 2H), 3.45 (t, 1H), 3.08 (m, 3H), 3.01 (m, 1H), 2.93 (m, 1H), 2.58 (m, 1H), 2.52 (m, 1H), 2.30 (s, 6H), 1.25 (s, 9H).

Provenance & Evidence