Tetrabutylammonium Fluoride → HCID 66756755, compound

HRID 1642603Notes

Reaction equation

HRID 1642603 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[S:18](=[O:20])(=[O:19])[N:17](CC[Si](C)(C)C)[C:16](=[O:27])[CH2:15]2)=[C:10]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[S:18](=[O:20])(=[O:19])[NH:17][C:16](=[O:27])[CH2:15]2)=[C:10]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66756800HCID 66756800, compound

Product 1

HCID 66756755HCID 66756755, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 5-(4-benzyl-2-benzyloxyphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (1.1 g, 2.16 mmol) and TBAF (1.0 M solution in THF, 4.0 mL, 4 mmol) is heated at 50° C. for 18 h. After THF is removed under reduced vacuum, KHCO3 solution (0.50 M, 10 mL) is added, followed by water (10-15 mL). The residue is allowed to coat the glassware and the water is decanted. The residue is washed with water (2×), and ether (1×). The residue is treated with 1N HCl solution and is extracted with EtOAc. The organic layer is then washed with water, dried with MgSO4 and concentrated to give the title compound as an orange oil.

Workup

  1. customAfter THF is removed under reduced vacuum, KHCO3 solution (0.50 M, 10 mL)
  2. additionis added
  3. customthe water is decanted
  4. washThe residue is washed with water (2×), and ether (1×)
  5. additionThe residue is treated with 1N HCl solution
  6. extractionis extracted with EtOAc
  7. washThe organic layer is then washed with water
  8. dry with materialdried with MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-53d7c8db306346f880d4256ef876d70b
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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