Tetrahydrofuran → HCID 131723796, compound

HRID 1861662Notes

Reaction equation

HRID 1861662 reaction equation
[C:1]([S:4][CH2:5][CH2:6][N:7]([CH2:29][CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:8]([NH:10][CH2:11][CH:12]([O:21][Si](C(C)(C)C)(C)C)[CH2:13][N:14]1[CH2:19][CH2:18]N(C)[CH2:16][CH2:15]1)=[O:9])(=[O:3])[CH3:2].C(=O)([O-])O.[Na+].O1CC[CH2:44][CH2:43]1>>[C:1]([S:4][CH2:5][CH2:6][N:7]([CH2:29][CH2:30][CH:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1)[C:8]([NH:10][CH2:11][CH:12]([OH:21])[CH2:13][N:14]1[CH2:15][CH2:16][CH:43]([CH3:44])[CH2:18][CH2:19]1)=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 516892Sodium BicarbonateHCID 88114885HCID 88114885, compound2×

Product 1

HCID 131723796HCID 131723796, compound

Procedure

1-[2-(Acetylthio) ethyl]-3-[(2RS)-2-(t-butyldimethyl siloxy)-3-(4-methyl-1-piperazinyl)propyl]-1-(2-cyclohexylethyl) urea (Compound 3-19, 748 mg) was dissolved in anhydrous tetrahydrofuran (1.4 ml) in the nitrogen gas atmosphere, followed by the addition of a 1M solution of fluorinated tetra-n-butyl ammonium fluoride in tetrahydrofuran (1.45 ml) to the resulting solution with stirring at room temperature and stirring the mixture over 2.5 days. Saturated aqueous solution of sodium hydrogen carbonate was added to the reaction solution and the resulting mixture was extracted with ethyl acetate. The resulting organic phase was washed with saturated aqueous solution of sodium hydrogen carbonate and then saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting oily product was purified by the silica gel column chromatography to thus give the title compound (Compound 5-1, 89 mg).

Workup

  1. stirringstirring the mixture over 2.5 days
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe resulting organic phase was washed with saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialsaturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oily product was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-5a62866175204b3194379c987ccc4229
Source dataset
uspto-grants-2003_03
Patent number
US06534499B2

Reaction notes

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