Methyl N-(triethylammoniosulfonyl)carbamate → HCID 68951933, compound

Participants

Reaction Steps

To a suspension of ethyl 7-aminocarbonyl-3-benzyloxy-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (273 mg, 0.733 mmol) in anhydrous THF under an atmosphere of nitrogen was added Burgess reagent ((methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt, 349 mg, 1.47 mmol). The reaction was stirred at room temperature for 2 hours and then heated to 50° C. for 45 minutes. Additional Burgess reagent (4.89 g, 10.26 mmol) was added in portions and the reaction was heated to 60° C. overnight. The solvent was removed in vacuo, and the resulting residue was partitioned between saturated aqueous NH4Cl and EtOAc. The layers were separated and the aqueous was extracted twice more with EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to afford the title product. 1H NMR (400 MHz, d6-DMSO) δ 7.49-7.47 (m, 2H), 7.40-7.31 (m, 3H), 6.23 (t, J=4.0 Hz, 1H), 5.23 (dd, J=10.8, 24.6 Hz, 2H), 4.33-4.23 (m, 3H), 4.13 (dd, J=3.8, 13.8 Hz, 1H), 3.09 (s, 3H), 1.27 (t, J=7.2 Hz, 3H); ES MS (M+H)=355.

Provenance & Evidence