Acetic Acid → HCID 22881721, compound

HRID 1793253Notes

Reaction equation

HRID 1793253 reaction equation
C1(C[NH:8][CH:9]([C@:18]2([CH2:33][OH:34])[O:22][C@@H:21]([N:23]3[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]3=[O:25])[CH2:20][C@@H:19]2[OH:32])NCC2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C>C(O)C.[Pd]>[NH2:8][CH2:9][C@:18]1([CH2:33][OH:34])[O:22][C@@H:21]([N:23]2[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:20][C@@H:19]1[OH:32]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86589976HCID 86589976, compound

Product 1

HCID 22881721HCID 22881721, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4′-C-(1,1′-diphenylmethylaminomethyl)thymidine (3) (0.65 g, 1.5 mmol) was dissolved in absolute ethanol (50 mL). Cyctohexene (12 mL), glacial acetic acid (5 mL) and 5%-palladium on charcoal (0.6 g) were added and the mixture heated under reflux with stirring. The solution was heated for 5 hours and then allowed to cool to ambient temperature. Palladium catalyst was removed by filtration through celite and the filtrate was concentrated under vacuum to give the crude title compound (4), which was used in the following step without further purification. ES +ve m/z 272(M+H)+, 242(M—CH2NH2)+. For an alternative synthesis of this compound see: Wang et al; Tetrahedron Letters 1996, 37, 6515–6518.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux
  3. temperatureThe solution was heated for 5 hours
  4. customPalladium catalyst was removed by filtration through celite
  5. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-dc05bdb0f53e4ab480962f2ffcda9a1e
Source dataset
uspto-grants-2006_07
Patent number
US07078499B2

Reaction notes

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