Tetrabutylammonium Fluoride → HCID 68842200, compound

HRID 660793Notes

Reaction equation

HRID 660793 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[N:24]1[CH2:28][C:27](=[O:29])[N:26](CC[Si](C)(C)C)[S:25]1(=[O:37])=[O:36])[CH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[N:24]1[CH2:28][C:27](=[O:29])[NH:26][S:25]1(=[O:37])=[O:36])[CH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68842500HCID 68842500, compound

Product 1

HCID 68842200HCID 68842200, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzyl}-benzonitrile (57 mg, 0.107 mmol) in THF (10 mL) is added TBAF (0.16 mL, 1.5 equiv) and the mixture is stirred at 60° C. for 2 h. The mixture is partitioned between EtOAc and 1N HCl. The organic phase is washed with 1N HCl and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue purified by column chromatography using a gradient of 0-40% EtOAc/hexane as eluent to give the title compound.

Workup

  1. customThe mixture is partitioned between EtOAc and 1N HCl
  2. washThe organic phase is washed with 1N HCl and brine
  3. dry with materialthen is dried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-fcfc05eb1ea84ef9b8df4d719f7cb5bc
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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