Sodium Bicarbonate → HCID 15171473, compound

HRID 1030568Notes

Reaction equation

HRID 1030568 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][N:20]([CH2:22][CH2:23][N:24]1[C:28](=[O:29])[CH:27]([CH2:30][CH2:31][CH2:32][O:33][Si](C(C)(C)C)(C)C)[S:26][CH:25]1[C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)[CH3:21].C([O-])(O)=O.[Na+]>O1CCCC1>[CH3:19][N:20]([CH2:22][CH2:23][N:24]1[C:28](=[O:29])[CH:27]([CH2:30][CH2:31][CH2:32][OH:33])[S:26][CH:25]1[C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)[CH3:21]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 14999123HCID 14999123, compound

Product 1

HCID 15171473HCID 15171473, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution (15 ml) of tetrabutylammonium fluoride in tetrahydrofuran was added dropwise to a solution of 3-dimethylaminoethyl-5-(3-t-butyldimethylsilyloxypropyl)-2-(3-pyridyl)thiazolidin-4-one (2.6 g, 6.02 mmol) of dry tetrahydrofuran (12 ml) under cooling with ice. Then the mixture was stirred at room temperature for 2 hours to complete the reaction. Saturated aqueous NaHCO3 (10 ml) was added dropwise to the product mixture, and the resulting aqueous layer was extracted 6 times with ethyl acetate. The extract was dried over MgSO4, and the solvent was removed under reduced pressure. The residual crude product was purified by medium-pressure liquid chromatography (Si-60® Art. 9385, eluent : hexane : ethanol : aqueous ammonia=3000:400:50), giving 3-dimethylaminoethyl-5-(3-hydroxypropyl)-2-(3-pyridyl)thiazolidin-4-one (1.7 g, 88% yield). IR (CHCl3) [cm-1 ]; 3400 (br), 1670, 1595, 1580, 1360. NMR (CDCl3) [δ ppm]; 2.16 (6 H, s), 4.10-4.15 (1 H, m), 5.86 (1 H, d, J=2 Hz).

Workup

  1. temperatureunder cooling with ice
  2. customthe reaction
  3. extractionthe resulting aqueous layer was extracted 6 times with ethyl acetate
  4. dry with materialThe extract was dried over MgSO4
  5. customthe solvent was removed under reduced pressure
  6. customThe residual crude product was purified by medium-pressure liquid chromatography (Si-60® Art. 9385, eluent : hexane : ethanol : aqueous ammonia=3000:400:50)

Sources & evidence

ORD record
ord-56b0f1fa63554ea8b71d2b6e9fff89ca
Source dataset
uspto-grants-1992_04
Patent number
US05106860

Reaction notes

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