Methyl N-(triethylammoniosulfonyl)carbamate → HCID 71598840, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-5-(2-acetylhydrazinecarbonyl)-1H-pyrrole-2-carboxylate (31) (155 mg, 0.56 mmol) and Burgess reagent (132 mg, 0.56 mmol) were dissolved in THF (2 mL). The mixture was heated in a microwave at 100° C. for 30 min and the volatiles removed in vacuo. The crude product was purified by silica gel chromatography (12 g, 0-30% EtOAc in isohexane) to afford ethyl 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrrole-2-carboxylate (UL1-087) (115 mg, 77%) as a colourless oil: m/z 540 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.51-7.46 (m, 2H), 7.43-7.31 (m, 8H), 7.18-7.12 (m, 2H), 6.93-6.87 (m, 2H), 5.17 (s, 2H), 5.07 (s, 2H), 4.02 (q, J=7.1 Hz, 2H), 3.78 (s, 3H), 2.35 (s, 3H), 1.01 (t, J=7.1 Hz, 3H).

Provenance & Evidence