HCID 68839001, compound → HCID 24968956, compound

HRID 660505Notes

Reaction equation

HRID 660505 reaction equation
C([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=[CH:11][C:10]=1[N:24]1[S:28](=[O:30])(=[O:29])[NH:27][C:26](=[O:31])[CH2:25]1)C1C=CC=CC=1>CCO.CC(O)=O.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=[CH:11][C:10]=1[N:24]1[S:28](=[O:30])(=[O:29])[NH:27][C:26](=[O:31])[CH2:25]1

Participants

4

Reactant 1

HCID 68839001HCID 68839001, compound

Product 1

HCID 24968956HCID 24968956, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

A solution of 5-[2-benzyloxy-4-((E)-3-phenylpropenyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (74 mg, 0.17 mmol) in 6 mL of EtOH/HOAc (4:2) is hydrogenated at 50 psi over 10% Pd/C (70 mg) for 18 h. The catalyst is filtered, the solvent is removed under reduced pressure and the residual oil purified by preparative HPLC to give the title compound as a solid: (M−1)−=345.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solvent is removed under reduced pressure
  3. customthe residual oil purified by preparative HPLC

Sources & evidence

ORD record
ord-09b94874bd5f400a9724bcbc1bd76426
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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