Potassium Carbonate → HCID 58504138, compound

HRID 2407787Notes

Reaction equation

HRID 2407787 reaction equation
[CH3:1][O:2][CH:3]([O:40][CH3:41])[CH2:4][N:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[O:39])[CH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[S:32][C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)=[N:30][CH:29]=2)[CH2:23][CH2:22]1)[C:6](=O)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][CH:3]([O:40][CH3:41])[CH2:4][N:5]1[C:12]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:18](=[O:39])[C:19]([CH2:20][CH:21]2[CH2:22][CH2:23][N:24]([CH2:27][C:28]3[S:32][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[N:30][CH:29]=3)[CH2:25][CH2:26]2)=[C:6]1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58504269HCID 58504269, compound

Product 1

HCID 58504138HCID 58504138, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound prepared in Example 324 (0.390 g) was suspended in methanol (7 mL) and potassium carbonate (0.093 g) added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure to afford the crude material, which was partitioned between ethyl acetate and water. The organics were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude product, which was purified by flash column chromatography (eluant: 5% (9:1 methanol/concentrated ammonium hydroxide)/ethyl acetate) to furnish the title compound (0.340 g) having the following physical properties.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford the crude material, which
  3. customwas partitioned between ethyl acetate and water
  4. washThe organics were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude product, which
  9. customwas purified by flash column chromatography (eluant: 5% (9:1 methanol/concentrated ammonium hydroxide)/ethyl acetate)

Sources & evidence

ORD record
ord-49ef056f675b4fb997e8a8f4bbb545c0
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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