HCID 66845240, compound → HCID 66845474, compound

HRID 219044Notes

Reaction equation

HRID 219044 reaction equation
[I-:1].[CH3:2][C:3]1([CH3:48])[O:8][C:7]2[CH:9]=[CH:10][C:11]([C@@H:13]([OH:47])[CH2:14][N:15](C(=O)OCC3C=CC=CC=3)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][C:27]3[CH:28]=[C:29]([N+:33]([CH3:36])([CH3:35])[CH3:34])[CH:30]=[CH:31][CH:32]=3)=[CH:12][C:6]=2[CH2:5][O:4]1>C(O)C.[Pd]>[I-:1].[CH3:2][C:3]1([CH3:48])[O:8][C:7]2[CH:9]=[CH:10][C:11]([C@@H:13]([OH:47])[CH2:14][NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][C:27]3[CH:28]=[C:29]([N+:33]([CH3:36])([CH3:35])[CH3:34])[CH:30]=[CH:31][CH:32]=3)=[CH:12][C:6]=2[CH2:5][O:4]1

Participants

4

Reactant 1

HCID 66845240HCID 66845240, compound

Product 1

HCID 66845474HCID 66845474, compoundYield 4.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-{12-[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]-13-oxo-15-phenyl-2,5,14-trioxa-12-azapentadec-1-yl}-N,N,N-trimethylbenzenaminium iodide (195 mg) in ethanol (15 ml) was hydrogenated over 10% palladium on carbon (194 mg) for 5 h. The mixture was filtered through celite and the solvent evaporated in vacuo. The residue was purified by mass directed autopreparative HPLC to give the title compound (7 mg). LCMS RT=2.13 min.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent evaporated in vacuo
  3. customThe residue was purified by mass

Sources & evidence

ORD record
ord-e52aa22b25e341a9aa6f0f1d8250ceba
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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