Sodium Methoxide → HCID 13020163, compound

HRID 1645962Notes

Reaction equation

HRID 1645962 reaction equation
C([O:9][C@H:10]1[C@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[CH:42]=[C:40]([CH3:41])[C:38](=[O:39])[NH:37][C:35]1=[O:36])(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[C@H:11]1([N:34]2[CH:42]=[C:40]([CH3:41])[C:38](=[O:39])[NH:37][C:35]2=[O:36])[O:12][C@H:13]([CH2:24][OH:25])[C@@H:14]([OH:15])[C@@H:10]1[OH:9]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 14375035HCID 14375035, compound

Product 1

HCID 13020163HCID 13020163, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2',3',5'-Tri-O-benzoyl-α-D-arabinofuranosyl)thymine (18.6 g, 32.6 mmol) was dissolved in dry methanol and adjusted to pH 11 (as indicated by moist pH test paper) with freshly prepared sodium methoxide. After being stirred overnight, the solution was treated with Dowex-50 H+ resin, filtered, and evaporated to dryness. The residue was washed with ethyl acetate and dried, giving a crude yield of 8.0 g (69%). This was used without further purification. Its identity as Compound II was established by the following:

Workup

  1. additionthe solution was treated with Dowex-50 H+ resin
  2. filtrationfiltered
  3. customevaporated to dryness
  4. washThe residue was washed with ethyl acetate
  5. customdried
  6. customgiving a crude yield of 8.0 g (69%)
  7. customThis was used without further purification

Sources & evidence

ORD record
ord-655ed2da2b8b4d62babcd9d45d4322f9
Source dataset
uspto-grants-1993_01
Patent number
US05177196

Reaction notes

Loading…