HCID 70871741, compound → HCID 68311087, compound

HRID 470710Notes

Reaction equation

HRID 470710 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH:15]=[CH:14][C@@H:13]([CH2:16][O:17][Si](C(C)(C)C)(C)C)[O:12][C@@H:10]1[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.C(O)C.[Pt](=O)=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:15][CH2:14][C@@H:13]([CH2:16][OH:17])[O:12][C@@H:10]1[CH3:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 70871741HCID 70871741, compound

Product 1

HCID 68311087HCID 68311087, compoundYield 79.7%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (960 mg, 2.68 mmol) obtained in Step 5 above was dissolved in ethyl acetate (5 ml) and ethanol (5 ml), platinum (IV) oxide (18 mg, 0.08 mmol) was added and the resulting mixture was stirred for 19 hours under hydrogen atmosphere. The catalyst was removed by filtration through celite, then the solvent in the filtrate was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=9:1→2:3 (v/v)] to give 524 mg (79%) of the title compound as a colorless solid.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe solvent in the filtrate was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=9:1→2:3 (v/v)]

Sources & evidence

ORD record
ord-7f478f3673614479b881ec37bb9a13e3
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

Loading…