Hydrochloric Acid → HCID 68838974, compound

HRID 660596Notes

Reaction equation

HRID 660596 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:29][CH2:30][C:31]([N:33]([CH:35]([CH3:37])[CH3:36])[CH3:34])=[O:32])[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.CCOC(C)=O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:29][CH2:30][C:31]([N:33]([CH:35]([CH3:37])[CH3:36])[CH3:34])=[O:32])[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:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 68839959HCID 68839959, compound

Product 1

HCID 68838974HCID 68838974, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-N-isopropyl-N-methylpropionamide (0.114 g, 0.2 mmol) in THF (2 mL) is added a 0.5M solution of TBAF (0.84 mL) in THF. The mixture is refluxed for 1 h, then allowed to cool to RT. To the mixture is added 1N HCl and EtOAc. The organic phase is washed with 1N HCl and sat. NaCl. The solution is dried over sodium sulfate and the solvent removed under reduced pressure to afford the title compound. This is used directly in the next step.

Workup

  1. temperatureThe mixture is refluxed for 1 h
  2. washThe organic phase is washed with 1N HCl and sat. NaCl
  3. dry with materialThe solution is dried over sodium sulfate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-700eeaaff22540d88d624a01c56cd8e7
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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