Water → HCID 23399178, compound

HRID 1062355Notes

Reaction equation

HRID 1062355 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([S:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33]C(C)(C)C)[C:28]=3O[SiH](C)C)=[CH:22][C:21]=2[Cl:42])[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([S:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=3)=[CH:22][C:21]=2[Cl:42])[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 131725198HCID 131725198, compound

Product 1

HCID 23399178HCID 23399178, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the compound of Example 33 (1.10 g) in THF (20 mL), a 1 mol/L solution of tetrabutylammonium fluoride in THF (5 mL) was added. After 10 minutes, the reaction mixture was poured into water and was extracted with ethyl acetate. The organic phase was sequentially washed with water and a saturated aqueous solution of sodium chloride and was dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain the desired product (900 mg) as a colorless powder.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic phase was sequentially washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride and was dried with anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-440e8d2c759a4324b316362ede0af625
Source dataset
uspto-grants-2005_11
Patent number
US06960692B2

Reaction notes

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