Tetrabutylammonium Fluoride → HCID 68842164, compound

HRID 660648Notes

Reaction equation

HRID 660648 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:29][CH2:30][NH:31][S:32]([CH2:35][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)(=[O:34])=[O:33])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[N:17](CC[Si](C)(C)C)[S:16]1(=[O:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:29][CH2:30][NH:31][S:32]([CH2:35][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)(=[O:33])=[O:34])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:27])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68997502N-(2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-ethyl)-C-cyclohexyl-methanesulfonamide

Product 1

HCID 68842164HCID 68842164, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-ethyl)-C-cyclohexyl-methanesulfonamide (0.106 g, 0.17 mmol) is dissolved in THF (3 mL) and TBAF (0.089 mg, 0.099 mL of 1N in THF, 0.34 mmol) is added. The mixture is refluxed for 30 min and then diluted with 1N HCl and extracted with EtOAc. The combined organic layers are washed with 1N HCl, dried over MgSO4 and evaporated to afford the title compound.

Workup

  1. temperatureThe mixture is refluxed for 30 min
  2. extractionextracted with EtOAc
  3. washThe combined organic layers are washed with 1N HCl
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-425b7e15afbb4af8a647309638b592bc
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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