Triethylamine → HCID 45377904, compound

HRID 2088336Notes

Reaction equation

HRID 2088336 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:28]2[C:22]([C:23](Cl)([N:25]=[CH:26][N:27]=2)[NH2:24])=[N:21][CH2:20]1)(=[O:3])[CH3:2].N[C:31]1[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1.C(N(CC)CC)C>C(O)C>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:28]2[N:27]=[CH:26][N:25]=[C:23]([NH:24][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=3)[C:22]=2[N:21]=[CH:20]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 115683-AminophenolHCID 86662596HCID 86662596, compound

Product 1

HCID 45377904HCID 45377904, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of O2′,O3′,O5′-tri-acetyl-6-chloroadenosine (5.4 g) in absolute ethanol (30 mL) were added 3-aminophenol (4.28 g) and dry triethylamine (3.96 g), and the mixture was refluxed 8 h at 60° C. The solution was allowed to cool and was concentrated in vacuo and the residue was chromatographed (ethyl acetate:petroleumether=2:1) to give O2′,O3′,O5′-tri-acetyl-N6-(3-hydroxylphenyl)adenosine as a white solid (1.51 g).

Workup

  1. temperatureto cool
  2. concentrationwas concentrated in vacuo
  3. customthe residue was chromatographed (ethyl acetate:petroleumether=2:1)

Sources & evidence

ORD record
ord-b3e931a7a7fd45df86909c6e31f6978f
Source dataset
uspto-grants-2013_05
Patent number
US08435962B2

Reaction notes

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