5-[2-Benzyloxy-4-(2-methoxymethylbenzyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one → 5-[2-Hydroxy-4-(2-methoxymethylbenzyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660799Notes

Reaction equation

HRID 660799 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][O:23][CH3:24])[CH:12]=[CH:11][C:10]=1[N:25]1[S:29](=[O:31])(=[O:30])[NH:28][C:27](=[O:32])[CH2:26]1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][O:23][CH3:24])[CH:12]=[CH:11][C:10]=1[N:25]1[S:29](=[O:31])(=[O:30])[NH:28][C:27](=[O:32])[CH2:26]1

Participants

4

Reactant 1

HCID 688385095-[2-Benzyloxy-4-(2-methoxymethylbenzyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 577774135-[2-Hydroxy-4-(2-methoxymethylbenzyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-[2-benzyloxy-4-(2-methoxymethylbenzyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (270 mg) in ethanol (5 mL) is hydrogenated over 5% Pd/C at 1 atm for 2 h. The catalyst is removed by filtration through Celite and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC to give the title compound. (M−1)−=361. HPLC retention time=1.01 min (Method A).

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. customthe solvent is removed under reduced pressure
  3. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-c74f5d501a534f5ca271a83c6840b1ce
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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