Potassium Carbonate → HCID 59627891, compound

HRID 1367675Notes

Reaction equation

HRID 1367675 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

HCID 11430Potassium CarbonateHCID 59627882HCID 59627882, compound

Product 1

HCID 59627891HCID 59627891, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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+).

Workup

  1. customEthanol was removed under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washwashed with saturated aqueous solution of ammonium chloride
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by flash column chromatography on silica (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-cb39d84ef0ec4fc78b2a60796288d23e
Source dataset
uspto-grants-2011_02
Patent number
US07893268B2

Reaction notes

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