Hydrochloric Acid → 5-{4-[(E)-2-(1-Benzenesulfonylpyrrolidin-2-yl)-vinyl]-2-benzyloxyphenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660655Notes

Reaction equation

HRID 660655 reaction equation
[C:1]1([S:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[S:27](=[O:29])(=[O:28])[N:26](CC[Si](C)(C)C)[C:25](=[O:36])[CH2:24]3)=[C:19]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:18]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[C:1]1([S:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:36])[CH2:24]3)=[C:19]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:18]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 688422695-{4-[(E)-2-(1-Benzenesulfonylpyrrolidin-2-yl)-vinyl]-2-benzyloxyphenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 688389905-{4-[(E)-2-(1-Benzenesulfonylpyrrolidin-2-yl)-vinyl]-2-benzyloxyphenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 5-{4-[(E)-2-(1-benzenesulfonylpyrrolidin-2-yl)-vinyl]-2-benzyloxyphenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (53 mg) in THF (2 mL) is added 0.2 mL of a 1M solution of TBAF in THF. The mixture is stirred at 60° C. for 2 h then is allowed to cool to RT. The mixture is poured into 1N HCl (20 mL) and extracted with EtOAc. The organic phase is washed with 1N HCl and brine and is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by reverse phase Biotage using a gradient of 0-100% EtOH/water as eluent to furnish the title compound as a blue oil: (M−1)−=548.

Workup

  1. temperatureto cool to RT
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with 1N HCl and brine
  4. dry with materialis dried 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-612a95e4f7ac45b7945daa36b7a37903
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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