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

HRID 660656Notes

Reaction equation

HRID 660656 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])[NH:26][C:25](=[O:30])[CH2:24]3)=[C:19]([O:31]CC3C=CC=CC=3)[CH:18]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.O.[Pd]>[C:1]1([S:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]3)=[C:19]([OH:31])[CH:18]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

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

Product 1

HCID 577773375-{4-[2-(1-Benzenesulfonylpyrrolidin-2-yl)-ethyl]-2-hydroxyphenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

To a mixture of 5-{4-[(E)-2-(1-benzenesulfonylpyrrolidin-2-yl)-vinyl]-2-benzyloxyphenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one (22 mg) in 4 mL ethanol/water (1:3) is added 5 mg of Degussa Pd/C and the resulting mixture is hydrogenated at 1 atm for 1 h. The catalyst is filtered through Celite and the solvent is removed under reduced pressure. The residue is purified by reverse phase Biotage using a gradient of 20-60% EtOH/water as eluent to furnish the title compound: LC retention time=1.10 min (Method A); (M−H)−=464.

Workup

  1. filtrationThe catalyst is filtered through Celite
  2. customthe solvent is removed under reduced pressure
  3. customThe residue is purified by reverse phase Biotage

Sources & evidence

ORD record
ord-2b6a06a85a4348d798c5bb4543702bd8
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…