HCID 67139934, compound → HCID 67138314, compound

HRID 1592008Notes

Reaction equation

HRID 1592008 reaction equation
C([O:8][C:9](=[O:36])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:21][C:20](=[O:22])[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=3[O:32][CH3:33])[S:18]2(=[O:35])=[O:34])=[CH:12][CH:11]=1)C1C=CC=CC=1.[H][H]>CCOC(C)=O.CCO.[Pd]>[CH3:33][O:32][C:25]1[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:24]=1[CH2:23][N:19]1[S:18](=[O:35])(=[O:34])[N:17]([CH2:16][C:13]2[CH:14]=[CH:15][C:10]([C:9]([OH:36])=[O:8])=[CH:11][CH:12]=2)[CH2:21][C:20]1=[O:22]

Participants

5

Reactant 2

HCID 67139934HCID 67139934, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67138314HCID 67138314, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

The title A compound, 4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid benzyl ester (2.04 g, 4.0 mmol) is suspended in EtOAc/EtOH (1:1, 100 mL) along with 10% palladium on carbon (300 mg) and treated with hydrogen (48 psi) for 4 h on a Parr Shaker. The reaction mixture is filtered through celite and concentrated to give a white solid which is recrystallized from MeOH to yield 4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid: [M-1]-=419.

Workup

  1. filtrationThe reaction mixture is filtered through celite and
  2. concentrationconcentrated
  3. customto give a white solid which
  4. customis recrystallized from MeOH

Sources & evidence

ORD record
ord-56bd0e5aa35a4eaa8736b940acd6304e
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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