Hydrochloric Acid → HCID 68838563, compound

HRID 660752Notes

Reaction equation

HRID 660752 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:29][CH2:30][CH2:31][C:32]#[N: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-].Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:29][CH2:30][CH2:31][C:32]#[N:33])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:28])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 68842371HCID 68842371, compound

Product 1

HCID 68838563HCID 68838563, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of 4-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-butyronitrile (45.7 mg, 0.094 mmol) in THF (4 mL) is added 0.188 mL of a 1M solution of TBAF in THF. The mixture is stirred at 65° C. for 1 h then is allowed to cool to RT. The mixture is poured into 1N HCl and extracted with EtOAc. The organic phase is washed with brine and dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by reverse phase Biotage using a gradient of 0-30% EtOH/water as eluent to furnish the title compound.

Workup

  1. temperatureto cool to RT
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by reverse phase Biotage

Sources & evidence

ORD record
ord-3cda9fdfa0ee484ab8151f2ba9f50bc2
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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