HCID 68353070, compound → HCID 68353170, compound

HRID 1844671Notes

Reaction equation

HRID 1844671 reaction equation
C([O:8][C:9]1[CH:13]([CH2:14][CH:15]2[CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17][CH2:16]2)[NH:12][C:11](=[O:23])[C:10]=1[C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[CH3:31])C1C=CC=CC=1>CO.[Pd]>[CH3:31][C:25]1[CH:26]=[CH:27][C:28]([CH3:30])=[CH:29][C:24]=1[C:10]1[C:11](=[O:23])[NH:12][CH:13]([CH2:14][CH:15]2[CH2:16][CH2:17][S:18](=[O:22])(=[O:21])[CH2:19][CH2:20]2)[C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 68353070HCID 68353070, compound

Product 1

HCID 68353170HCID 68353170, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (50 mg) was added to a solution of 4-benzyloxy-3-(2,5-dimethyl-phenyl)-5-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-ylmethyl)-1,5-dihydro-pyrrol-2-one (280 mg, 0.64 mmol) in 20 ml of methanol and the mixture was hydrogenated for 2 h. Then, the resulting mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by flash chromatography on silica gel. Yield: 200 mg of 3-(2,5-dimethyl-phenyl)-5-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-ylmethyl)-4-hydroxy-1,5-dihydro-pyrrol-2-one (title compound P2.6) as a solid, mp 244-246° C.

Workup

  1. filtrationThen, the resulting mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-fe0db49106564230a817f27d668d07b6
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

Loading…