Tetrabutylammonium Fluoride → HCID 9851658, compound

HRID 2268368Notes

Reaction equation

HRID 2268368 reaction equation
[Si]([O:8][C@@H:9]1[C@H:13]([O:14][Si](C(C)(C)C)(C)C)[C@@H:12]([CH2:22][O:23][CH3:24])[O:11][C@H:10]1[N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][C:28]([CH2:49][CH2:50][NH:51][CH2:52][CH:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1)=[N:29][C:30]=2[NH:34][CH2:35][CH:36]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:53]1([CH2:52][NH:51][CH2:50][CH2:49][C:28]2[N:27]=[C:26]3[C:31]([N:32]=[CH:33][N:25]3[C@H:10]3[C@H:9]([OH:8])[C@H:13]([OH:14])[C@@H:12]([CH2:22][O:23][CH3:24])[O:11]3)=[C:30]([NH:34][CH2:35][CH:36]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:29]=2)[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69534139HCID 69534139, compound

Product 1

HCID 9851658HCID 9851658, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{2-[(cyclohexylmethyl)amino]ethyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine (210 mg, 0.25 mmol) (preparation 23) was dissolved in stirred tetrahydrofuran (1 ml) and a 1M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (1 ml, 1 mmol) added. The reaction mixture was stirred at room temperature for 24 hr. The solvent was removed under reduced pressure and the residue partitioned between dilute aqueous sodium hydroxide solution and ethyl acetate. The organic layer was separated and the aqueous phase extracted with ethyl acetate. The ethyl acetate phases were combined and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (94:6:0.6) increasing in polarity to (91:9:0.9). This gave the title compound (70 mg) as a powder. MS: 601 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between dilute aqueous sodium hydroxide solution and ethyl acetate
  3. customThe organic layer was separated
  4. extractionthe aqueous phase extracted with ethyl acetate
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (94:6:0.6)
  8. temperatureincreasing in polarity to (91:9:0.9)

Sources & evidence

ORD record
ord-1bb458b4288f45ebb30f42a07cc2a7b9
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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