5-[2-Benzyloxy-4-(hydroxypyridin-2-yl-methyl)-phenyl]1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one → 5-[2-Benzyloxy-4-(pyridine-2-carbonyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

HRID 660810Notes

Reaction equation

HRID 660810 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:15]([OH:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:12]=[CH:11][C:10]=1[N:23]1[S:27](=[O:29])(=[O:28])[N:26]([CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:25](=[O:36])[CH2:24]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.CCOC(C)=O.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[O:22])[CH:12]=[CH:11][C:10]=1[N:23]1[S:27](=[O:28])(=[O:29])[N:26]([CH2:30][CH2:31][Si:32]([CH3:34])([CH3:33])[CH3:35])[C:25](=[O:36])[CH2:24]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 688429995-[2-Benzyloxy-4-(hydroxypyridin-2-yl-methyl)-phenyl]1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 688431205-[2-Benzyloxy-4-(pyridine-2-carbonyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[2-benzyloxy-4-(hydroxypyridin-2-yl-methyl)-phenyl]1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (45 mg, 0.085 mmol) in acetic acid (2 mL) is added iron powder (24 mg, 0.43 mmol) and the mixture is refluxed for 2 h. The reaction is diluted with EtOAc and filtered. The solvent is removed under reduced pressure and the crude material is purified by flash chromatography using a gradient of 0-50% EtOAc/hexane to afford the title compound as a yellow oil: (M+H)+=524.

Workup

  1. temperaturethe mixture is refluxed for 2 h
  2. filtrationfiltered
  3. customThe solvent is removed under reduced pressure
  4. customthe crude material is purified by flash chromatography

Sources & evidence

ORD record
ord-d1f799d30ee7451786bc8d83af4c454b
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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