Water → 5-{2-Hydroxy-4-[1-(2,4,6-trimethylphenyl)-ethyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660780Notes

Reaction equation

HRID 660780 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH:15]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[CH3:16])[CH:12]=[CH:11][C:10]=1[N:26]1[S:30](=[O:32])(=[O:31])[NH:29][C:28](=[O:33])[CH2:27]1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].O>CCO.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([CH:15]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[CH3:16])[CH:12]=[CH:11][C:10]=1[N:26]1[S:30](=[O:32])(=[O:31])[NH:29][C:28](=[O:33])[CH2:27]1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 688433595-{2-Benzyloxy-4-[1-(2,4,6-trimethylphenyl)-ethyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 577773645-{2-Hydroxy-4-[1-(2,4,6-trimethylphenyl)-ethyl]-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-[1-(2,4,6-trimethylphenyl)-ethyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one and K2CO3 (60 mg) in EtOH (5 mL)/water (7 mL) is hydrogenated at 1 atm over 10% Pd/C (50 mg) for 10 days. The catalyst is filtered and the solvent evaporated to give the title compound as a pale-yellow solid: (M−1)−=373. HPLC retention time: 1.45 min (Method A).

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-02072fd60e104a0492d158cae8aa80a5
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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