反应详情

To a 200 mL round bottomed flask with a stirring bar and an argon inlet was added 5-phenyl-1H-pyrrole-2-carboxylic acid AV-5-1 (2.45 g, 13.09 mmol), N,O-dimethylhydroxylamine hydrochloride (1.40 g, 14.40 mmol), N-ethyl-N′-dimethylaminopropylcarbodiimide hydrochloride (2.76 g, 14.40 mmol), hydroxybenztriazole hydrate (1.94 g, 14.40 mmol) and dry, degassed DMF (25 mL). This well stirred mixture was warmed gently until all of the solids dissolved. Et3N (5.6 mL, 40.00 mmol) was added in one portion. The resulting mixture was stirred at ambient temperature 18 h. The solvents were removed in vacuo at +80° C. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc. The layers were separated and the organic phase was washed with H2O (2×) and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave a solid. This material was chromatographed on silica gel using 35% EtOAc in hexane as eluant to give 5-phenyl-1H-pyrrole-2-carboxylic acid methoxymethylamide AV-6-1 as a solid. 1H NMR (CDCl3) δ 3.36 (3H, s), 3.80 (3H, s), 6.58 (1H, dd, j=2.2, 4.0 Hz), 6.94 (1H, dd, j=2.2, 4.0 Hz), 7.30 (1H, m), 7.41 (2H, m), 7.58 (2H, m), 9.63 (1H, br s).

1. customdry
2. customdegassed DMF (25 mL)
3. temperaturewas warmed gently until all of the solids
4. dissolutiondissolved
5. stirringThe resulting mixture was stirred at ambient temperature 18 h
6. customThe solvents were removed in vacuo at +80° C
7. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc
8. customThe layers were separated
9. washthe organic phase was washed with H2O (2×) and brine
10. customDrying
11. filtration(MgSO4), filtration and removal of the solvent in vacuo
12. customgave a solid
13. customThis material was chromatographed on silica gel using 35% EtOAc in hexane as eluant