Tetrabutylammonium Fluoride → HCID 25143686, compound

HRID 452246Notes

Reaction equation

HRID 452246 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:36][CH2:37][C:38]1[C:39](=[O:67])[N:40]([C:44]2[CH:49]=[CH:48][C:47]([N:50]3[CH2:54][C@H:53]([CH2:55][NH:56][C:57]([C:59]4[S:60][C:61]([Cl:64])=[CH:62][CH:63]=4)=[O:58])[O:52][C:51]3=[O:65])=[CH:46][C:45]=2[Cl:66])[CH:41]=[CH:42][CH:43]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.O.[Cl-].[Na+].C(OCC)(=O)C>[Cl:64][C:61]1[S:60][C:59]([C:57]([NH:56][CH2:55][C@@H:53]2[O:52][C:51](=[O:65])[N:50]([C:47]3[CH:48]=[CH:49][C:44]([N:40]4[CH:41]=[CH:42][CH:43]=[C:38]([CH2:37][OH:36])[C:39]4=[O:67])=[C:45]([Cl:66])[CH:46]=3)[CH2:54]2)=[O:58])=[CH:63][CH:62]=1

Participants

7

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59410211HCID 59410211, compound

Product 1

HCID 25143686HCID 25143686, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

367 mg (1.41 mmol; 1 molar in THF) of tetrabutylammonium fluoride are added to a solution of 515 mg (0.703 mmol) of the compound from Example 6A in 8 ml of THF. After 3 h at RT, the mixture is diluted with water, saturated aqueous sodium chloride solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate, and the combined organic phases are dried over sodium sulphate. After filtration, the mixture is freed from the solvent and the residue is purified by chromatography on silica gel (dichloromethane/methanol 20:1). This gives 278 mg (78% of theory) of the desired product.

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. dry with materialthe combined organic phases are dried over sodium sulphate
  3. filtrationAfter filtration
  4. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 20:1)

Sources & evidence

ORD record
ord-ff7e7cbdc4b74164ac4e11cc4bd8404b
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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