Methanol → HCID 178507181, compound

HRID 1029381Notes

Reaction equation

HRID 1029381 reaction equation
[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].CO.ClC1C=C(C=CC=1)C(OO)=[O:27]>C(OCC)(=O)C>[C@@H:1]1([N:10]2[C:19]3[C:13](=[C:14]([N+:16]([O-:27])=[CH:17][N:18]=3)[NH2:15])[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 60961AdenosineHCID 70297m-Chloroperbenzoic acid3×

Product 1

HCID 178507181HCID 178507181, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 1-L round-bottomed flask protected with a calcium sulfate drying tube was placed a 5.0 g (18.7 mmol) of adenosine and 500 mL of methanol. The mixture was stirred at room temperature and 4.85 g (22.5 mmol) of m-chloroperoxybenzoic acid (MCPBA) was added in 7-10 portions over 2 hours. If thin-layer chromatography after 15-20 hours of stirring indicates the presence of starting material an additional 0.5 g (2.9 mmol) of MCPBA should be added and the reaction stirred an additional 4 hours. If the TLC continues to show starting material another portion of MCPBA must be added and the stirring continued overnight. After the TLC showed little or no starting material left the reaction mixture was poured slowly in 2 L of ethyl acetate with good stirring. After having been stirred 2 hours, the product was collected, washed with ethyl acetate, and dried in vacuo over phosphorus pentoxide: yield 4.6 g. Melting point and elemental analysis data are set forth in Table I.

Workup

  1. customIn a 1-L round-bottomed flask protected with a calcium sulfate drying tube
  2. stirringIf thin-layer chromatography after 15-20 hours of stirring
  3. additionshould be added
  4. stirringthe reaction stirred an additional 4 hours
  5. additionmust be added
  6. customthe stirring continued overnight
  7. waitno starting material left the reaction mixture
  8. stirringAfter having been stirred 2 hours
  9. customthe product was collected
  10. washwashed with ethyl acetate
  11. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-11d4964238224a9cacc2d57b7ded39f9
Source dataset
uspto-grants-1992_04
Patent number
US05102873

Reaction notes

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