Sodium Bicarbonate → HCID 18922037, compound

HRID 1289814Notes

Reaction equation

HRID 1289814 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][C:20]([CH3:53])=[CH:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:31](=[O:52])[C:32]([CH:47]2[CH2:51][CH2:50][CH2:49][CH2:48]2)([OH:46])[C:33]2[NH:34][CH:35]=[C:36](COCC[Si](C)(C)C)[N:37]=2)[CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:19][C:20]([CH3:53])=[CH:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:31](=[O:52])[C:32]([C:33]2[NH:37][CH:36]=[CH:35][N:34]=2)([CH:47]2[CH2:48][CH2:49][CH2:50][CH2:51]2)[OH:46])[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 178444688HCID 178444688, compound

Product 1

HCID 18922037HCID 18922037, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.3 ml of a 1N tetrabutylammonium fluoride solution in tetrahydrofuran was added to a solution of 44 mg of N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-cyclopentyl-2-hydroxy-2-{[2-(trimethylsilyl)ethoxymethyl]imidazol-2-yl}acetamide in 2 ml of tetrahydrofuran at 60° C., and this mixture was stirred at the same temperature for 5 hours. The reaction mixture was mixed with a saturated aqueous solution of sodium bicarbonate and extracted with diethyl ether. The organic layer was washed with water and a saturated aqueous solution sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by preparative thin layer chromatography [Kieselgel™ 60F254, Art 5744 (manufactured by E. Merck); developing solvent: chloroform/methanol=7/1] to obtain 14 mg of the title compound.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution sodium chloride and then dried over anhydrous magnesium sulfate
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by preparative thin layer chromatography [Kieselgel™ 60F254, Art 5744 (manufactured by E. Merck); developing solvent: chloroform/methanol=7/1]

Sources & evidence

ORD record
ord-5bd432d2285140fea6e8d8fc776bb483
Source dataset
uspto-grants-1998_05
Patent number
US05750540

Reaction notes

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