Sodium ethoxide → HCID 54008737, compound

HRID 1167031Notes

Reaction equation

HRID 1167031 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[C:34]1[S:35][CH:36]=[C:37]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[N:38]=1)(=O)C1C=CC=CC=1.[O-]CC.[Na+]>C(O)C>[C@@H:11]1([C:34]2[S:35][CH:36]=[C:37]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[N:38]=2)[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 2723922Sodium ethoxideHCID 11146426HCID 11146426, compound

Product 1

HCID 54008737HCID 54008737, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude ethyl-(2′,3′,5′-tri-O benzoyl-β-D-ribofiuranosyl)thiazole-4-carboxylate (4, 15.00 g) was dissolved in dry ethanol (100 ml) and treated with sodium ethoxide powder (1.36 g, 20 mmol) under argon atmosphere. The reaction mixture was stirred at room temperature for 12 hr under argon. The solution was neutralized with Dowex 50W-X8 H+ resin, filtered and washed with methanol (100 ml). The filtrate was evaporated to dryness. The residue was partitioned between water (100 ml) and chloroform (I50 ml). The aqueous layer was washed with chloroform (100 ml) and evaporated to dryness. The residue was dissolved in methanol (100 ml), silica gel (15 g) was added and evaporated to dryness. The dried compound adsorbed silica gel was placed on top of the silica column (5×20 cm) packed in CH2Cl2. The column was eluted with CH2Cl2/acetone (7:3; 500 ml) followed by CH2Cl2/methanol(95:5; 1000 ml). The CH2 C12/methanol fractions were collected together and evaporated to give pure 5. A small amount was crystallized from 2-propanol/ether as colorless product. Yield 4.8 g (83%); mp 62-64° C. 1H NMR (DMSO-d6); δ 1.36 (t, 3 H), 3.52 (m; 2 H), 3.84 (m, 2 H), 4.06 (m, I H), 4.28 (m, 2 H), 4.94 (t, 1H), 4.98 (d, 1 H), 5.08 (d, I H), 5.46 (d, I H) and 8.52 (s, 1 H).

Workup

  1. filtrationfiltered
  2. washwashed with methanol (100 ml)
  3. customThe filtrate was evaporated to dryness
  4. customThe residue was partitioned between water (100 ml) and chloroform (I50 ml)
  5. washThe aqueous layer was washed with chloroform (100 ml)
  6. customevaporated to dryness
  7. dissolutionThe residue was dissolved in methanol (100 ml)
  8. additionsilica gel (15 g) was added
  9. customevaporated to dryness
  10. washThe column was eluted with CH2Cl2/acetone (7:3; 500 ml)
  11. customThe CH2 C12/methanol fractions were collected together
  12. customevaporated
  13. customto give pure 5
  14. customA small amount was crystallized from 2-propanol/ether as colorless product

Sources & evidence

ORD record
ord-cd49551e362c421d9daecaff10f9bc3a
Source dataset
uspto-grants-2003_09
Patent number
US06613896B1

Reaction notes

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