Potassium Carbonate → HCID 59393706, compound

HRID 2092132Notes

Reaction equation

HRID 2092132 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:18]=[N:19][C:20]([C:23]([C:28]3[CH:33]=[CH:32][C:31]([C:34]4[CH:35]=[N:36][CH:37]=[C:38]([O:40][CH3:41])[CH:39]=4)=[CH:30][CH:29]=3)([CH3:27])[CH:24]([CH3:26])[CH3:25])=[CH:21][CH:22]=2)[N:13]=1)(=O)C.C(=O)(O)[O-].[Na+]>O.CO>[CH3:41][O:40][C:38]1[CH:39]=[C:34]([C:31]2[CH:32]=[CH:33][C:28]([C:23]([C:20]3[N:19]=[CH:18][C:17]([C:14]4[N:13]=[C:12]([CH2:11][OH:10])[O:16][N:15]=4)=[CH:22][CH:21]=3)([CH3:27])[CH:24]([CH3:25])[CH3:26])=[CH:29][CH:30]=2)[CH:35]=[N:36][CH:37]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 59393695HCID 59393695, compound

Product 1

HCID 59393706HCID 59393706, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of potassium carbonate (743 mg, 5.38 mmol) in water (1.00 mL) was added to a stirred solution of 1c (0.896 mmol) in methanol (3.00 mL) at rt. After approximately 1 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-6% methanol/DCM as eluent) to furnish the title compound 1d. m/z (ES) 431 (MH)+. 1HNMR (500 MHz, CD3OD): δ 9.19 (d, 1H, J=2.1 Hz), 8.65 (d, 1H, J=1.4 Hz), 8.46 (d, 1H, J=2.5 Hz), 8.32 (dd, 1H, J=2.2, 8.5 Hz), 8.24 (m, 1H), 7.72 (d, 2H, J=8.4 Hz), 7.62 (d, 2H, J=8.4 Hz), 7.59 (d, 1H, J=8.7 Hz), 4.88 (s, 2H), 4.07 (s, 3H), 3.24 (m, 1H), 1.80 (s, 3H), 0.91 (d, 3H, J=6.6 Hz), 0.87 (d, 3H, J=6.8 Hz).

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-6% methanol/DCM as eluent)

Sources & evidence

ORD record
ord-9412d8f906ea4f2f89b675be5cb4be5d
Source dataset
uspto-grants-2013_05
Patent number
US08440672B2

Reaction notes

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