Ethanol → HCID 178464535, compound

HRID 991154Notes

Reaction equation

HRID 991154 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+]=[N-].CCO.C(N(CC)C(C)C)(C)C.[CH3:32][C:33]([CH:35]1[C:41](=[O:42])[CH2:40][C:39]([CH3:44])([CH3:43])[CH2:38][C:36]1=[O:37])=O>CO.[Pd]>[CH3:44][C:39]1([CH3:43])[CH2:40][C:41](=[O:42])[C:35](=[C:33]([NH:1][C@@H:4]2[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]3[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]3=[O:13])[CH2:5]2)[CH3:32])[C:36](=[O:37])[CH2:38]1

Participants

7

Reactant 4

HCID 702EthanolHCID 35370ZidovudineHCID 81531DiisopropylethylamineHCID 5194481,3-Cyclohexanedione, 2-acetyl-5,5-dimethyl-

Product 1

HCID 178464535HCID 178464535, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3′-Deoxy-3′-azido-thymidine (200 mg, 0.75 mmol) was dissolved in MeOH (25 ml) and Pd/C (40 mg) was added. The suspension was stirred over a constant stream of H2 overnight. The reaction mixture was filtered, and the filtrate was concentrated. The residue was taken up in abs. EtOH (5 ml), N,N-diisopropylethylamine (0.1 ml) and 2-acetyldimedone (204 mg, 1.12 mmol) were added and the solution was refluxed for 5 h. The reaction mixture was cooled to room temperature and the product was precipitated by adding ether (50 ml) giving 3′-deoxy-3′-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-thymidine (24) (200 mg, 66%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. temperaturethe solution was refluxed for 5 h
  4. customthe product was precipitated
  5. additionby adding ether (50 ml)

Sources & evidence

ORD record
ord-ec9fdee397b346fd96d26abcf130b5e9
Source dataset
uspto-grants-2002_10
Patent number
US06462183B1

Reaction notes

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