Methyl N-(triethylammoniosulfonyl)carbamate → HCID 57550206, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of methyl N-{4-[(1-methyl-1H-benzimidazol-2-yl)methyl]-benzoyl}-serinate (0.2 g, 0.55 mmol, 1.0 eq) in THF was treated with Burgess reagent (0.156 g, 0.65 mmol) and molecular sieves (1 g), stirred at 60° C. for 2 h, cooled to room temperature and concentrated under reduced pressure. The resultant residue was purified by column chromatography (silica, CHCl3:MeOH 5%) to afford the title compound in 52% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, DMSO-d6): 7.95 (s, 1H), 7.84 (d, J=8 Hz, 1H), 7.57 (d, J=8 Hz, 1H), 7.48 (d, J=8 Hz, 1H), 7.39 (d, J=8 Hz, 2H)), 7.16-7.21 (m, 1H), 5.60 (m, 1H), 4.95 (t, J=8.4 Hz, 1H), 4.57-4.60 (m, 1H), 4.38 (s, 2H), 4.26 (t, J=8.4 Hz, 1H), 3.78 (s, 3H). LCMS (ESI+) 350 (MH+).

Provenance & Evidence