Potassium Fluoride → HCID 57804506, compound

HRID 2104468Notes

Reaction equation

HRID 2104468 reaction equation
[F-].[K+].[CH3:3][C:4]1[O:8][C:7]([C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:32])[C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]#[C:27][Si](C)(C)C)=[CH:22][N:21]=3)=[O:18])[C@H:11]([NH:33][C:34]([C:36]3[S:37][C:38]4[CH2:39][N:40]([CH3:45])[CH2:41][CH2:42][C:43]=4[N:44]=3)=[O:35])[CH2:10]2)=[N:6][N:5]=1>CO>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:17](=[O:18])[C:16]([NH:15][C@H:12]2[CH2:13][CH2:14][C@H:9]([C:7]3[O:8][C:4]([CH3:3])=[N:5][N:6]=3)[CH2:10][C@H:11]2[NH:33][C:34]([C:36]2[S:37][C:38]3[CH2:39][N:40]([CH3:45])[CH2:41][CH2:42][C:43]=3[N:44]=2)=[O:35])=[O:32])=[N:21][CH:22]=1)#[CH:27]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 57804543HCID 57804543, compound

Product 1

HCID 57804506HCID 57804506, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium fluoride (116 mg) was added to a solution of the compound obtained in Example 401 (617 mg) in methanol (30 mL), and the mixture was stirred for 7 hours at room temperature. The solvent was removed under reduced pressure, and methylene chloride and water were added to the residue to partition the mixture. The organic layer was dried over sodium sulfate anhydrate, and the solvent was removed under reduced pressure. The residue was purified through silica gel flash column chromatography (methylene chloride:methanol=93:7). The thus-obtained solid was dissolved in methanol, water was added thereto, and the solvent was removed under reduced pressure, to thereby yield the title compound (287 mg).

Workup

  1. customThe solvent was removed under reduced pressure, and methylene chloride and water
  2. additionwere added to the residue
  3. customto partition the mixture
  4. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified through silica gel flash column chromatography (methylene chloride:methanol=93:7)
  7. dissolutionThe thus-obtained solid was dissolved in methanol
  8. additionwater was added
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4b11676e52874245b115a2241db5b53b
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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