Tetrabutylammonium Fluoride → HCID 67214791, compound

HRID 270505Notes

Reaction equation

HRID 270505 reaction equation
[Si]([O:18][C@@H:19]([CH3:51])[C:20]([N:22]1[N:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[S:24][C:23]1([CH2:40][CH2:41][CH2:42][NH:43][C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:21])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C([O-])(O)=O.[Na+]>[F:33][C:29]1[CH:28]=[C:27]([C:25]2[S:24][C@@:23]([CH2:40][CH2:41][CH2:42][NH:43][C:44](=[O:50])[O:45][C:46]([CH3:48])([CH3:47])[CH3:49])([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:22]([C:20](=[O:21])[C@@H:19]([OH:18])[CH3:51])[N:26]=2)[CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67214724HCID 67214724, compound

Product 1

HCID 67214791HCID 67214791, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a cooled (0° C.) solution of tert-butyl 3-(3-((S)-2-(tert-butyldiphenylsilyloxy)propanoyl)-5-(3-fluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propylcarbamate (180 mg, 0.25 mmol) in THF (2.5 mL) was added TBAF (0.40 mL of 1M solution in THF). After stirring at room temperature for 2 hours, the volume was reduced in vacuo and the mixture was diluted with half-saturated NaHCO3 (30 mL). The mixture was extracted with ethyl acetate (3×20 mL) and the combined organics were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed (30% ethyl acetate in hexanes) to provide the product (95 mg, 79%) as a viscous, yellow syrup.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  2. washthe combined organics were washed with brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7fde10c3918a4f68a67212c954f3ee22
Source dataset
uspto-grants-2008_11
Patent number
US07449486B2

Reaction notes

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