Ammonia → 2'-Deoxy-4'-C-ethynyl-2-fluoroadenosine

HRID 1863858Notes

Reaction equation

HRID 1863858 reaction equation
C([O:4][C@@H:5]1[C@@:9]([C:15]#[CH:16])([CH2:10][O:11]C(=O)C)[O:8][C@@H:7]([N:17]2[C:26]3[N:25]=[C:24]([F:27])[N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[CH:18]2)[CH2:6]1)(=O)C.N>CO>[C:15]([C@:9]1([CH2:10][OH:11])[O:8][C@@H:7]([N:17]2[C:26]3[N:25]=[C:24]([F:27])[N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[CH:18]2)[CH2:6][C@@H:5]1[OH:4])#[CH:16]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 866007813', 5'-di-O-acetyl-2'-deoxy-4'-C-ethynyl-2-fluoroadenosine

Product 1

HCID 64834312'-Deoxy-4'-C-ethynyl-2-fluoroadenosine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 3 (200 mg, 0.53 mmol) was dissolved in methanol (7.00 ml), and 28% aqueous ammonia (5.00 ml) was added to the resultant solution, followed by stirring at room temperature for four hours. The resultant reaction mixture was concentrated under reduced pressure, and a mixture of chloroform and methanol (20:1) was added to the resultant residue. The thus-precipitated crystals were filtered, and then the resultant crystals were recrystallized from water, to thereby yield compound 4 (113 mg, 0.39 mmol, 73.6%).

Workup

  1. customThe resultant reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. additiona mixture of chloroform and methanol (20:1)
  4. additionwas added to the resultant residue
  5. filtrationThe thus-precipitated crystals were filtered
  6. customthe resultant crystals were recrystallized from water

Sources & evidence

ORD record
ord-0882813f51584fe7be2104a310ff0d3f
Source dataset
uspto-grants-2009_12
Patent number
US07625877B2

Reaction notes

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