Potassium Carbonate → HCID 59627891, compound
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]([C@@H:12]1[CH2:16][C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=2)=[C:14]([CH3:24])[C@H:13]1[O:25]C(=O)C)=[O:11])[CH3:8]>C(O)C>[CH2:7]([O:9][C:10]([C@@H:12]1[CH2:16][C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=2)=[C:14]([CH3:24])[C@H:13]1[OH:25])=[O:11])[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Anhydrous potassium carbonate (45.6 mg, 0.33 mmol) was added to a solution of 92 (100 mg, 0.33 mmol) in dry ethanol (2.8 ml) at 0° C. and the solution was stirred at room temperature for 12 hr. Ethanol was removed under reduced pressure and the residue was dissolved in methylene chloride and washed with saturated aqueous solution of ammonium chloride. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed in vacuo. The residue was purified by flash column chromatography on silica (25% EtOAc/hexane) to give compound 88 (81 mg, 94%, 99% ee) as a pale yellow oil: [α]20D=−8.1 (c=0.26, CHCl3); TLC Rf=0.27 (silica gel, 75% EtOAc/hexanes); 1H NMR (C6D6, 600 MHz) δ 8.69 (s, 1H), 6.89-6.83 (m, 2H), 4.57 (s, 1H), 3.38-3.34 (m, 2H), 2.40-2.38 (m, 2H), 2.16-2.11 (m, 1H); 13C NMR (CDCl3, 100 MHz) δ 174.602, 153.069, 149.938, 138.385, 136.681, 134.969, 131.441, 122.385, 84.064, 61.037, 51.692, 35.927, 18.483, 14.518, 13.070. HRMS calcd for C15H19NO3+Na+ 284.1263; found 284.1279 (M+Na+).