Water → HCID 59837315, compound

HRID 272288Notes

Reaction equation

HRID 272288 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])([CH2:33][O:34][Si](C(C)(C)C)(C)C)[CH2:25][O:26][P:27]([O:31][CH3:32])([O:29][CH3:30])=[O:28])=[C:18]([Cl:50])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([NH:42][C:43]([O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[O:44])([CH2:33][OH:34])[CH2:25][O:26][P:27]([O:29][CH3:30])([O:31][CH3:32])=[O:28])=[C:18]([Cl:50])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67077272HCID 67077272, compound

Product 1

HCID 59837315HCID 59837315, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a THF solution (30 mL) of the compound of Example 243 (2.70 g), 1 mol/L tetrabutylammonium fluoride in THF (5 mL) was added and the mixture was stirred for 1 hour at room temperature. Following addition of water, the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and the organic phase was dried over anhydrous sodium sulfate. The solvent was removed by distillation and the residue was purified on a silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain the desired product as a colorless oil (2.30 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation
  5. customthe residue was purified on a silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-389de3765609476b918835bf91c96b2d
Source dataset
uspto-grants-2008_11
Patent number
US07456157B2

Reaction notes

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