Tetrahydrofuran → HCID 136005869, compound

HRID 915990Notes

Reaction equation

HRID 915990 reaction equation
O1CCCC1.[Si]([O:13][C@@H:14]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[NH:26][C:27](=[O:41])[C:28]4[N:33]([CH:34]5[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]5)[N:32]=[C:31]([CH3:40])[C:29]=4[N:30]=3)=[C:21]([O:42][CH3:43])[CH:20]=2)[CH2:15]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[CH:34]1([N:33]2[C:28]3[C:27](=[O:41])[NH:26][C:25]([C:22]4[CH:23]=[CH:24][C:19]([N:16]5[CH2:17][CH2:18][C@@H:14]([OH:13])[CH2:15]5)=[CH:20][C:21]=4[O:42][CH3:43])=[N:30][C:29]=3[C:31]([CH3:40])=[N:32]2)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 136005797HCID 136005797, compound

Product 1

HCID 136005869HCID 136005869, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 3 ml tetrahydrofuran solution of 243 mg (0.452 mmol) of the compound obtained in Example 269, 0.54 ml of tetrabutylammonium fluoride (1.0M tetrahydrofuran solution 0.54 mmoml) was added, and the mixture was stirred at room temperature for 2 hours. Then, water was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, whereafter the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol=30/1˜20/1) to obtain 191 mg (quant.) of the captioned compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, whereafter the solvent
  4. distillationwas distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol=30/1˜20/1)
  6. customto obtain 191 mg (quant.) of the captioned compound

Sources & evidence

ORD record
ord-b27d9f8baa9e4e85aa92bef2ae46682b
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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