Methanol → HCID 18394993, compound

HRID 1602971Notes

Reaction equation

HRID 1602971 reaction equation
[H-].[Na+].CO.[CH2:5]([C:7]1[C:8](=[S:47])[NH:9][C:10](=[O:46])[N:11]([CH:45]=1)[C@@H:12]1[O:44][C@H:33]([CH2:34][O:35]C(=O)C2C=CC=CC=2)[C@@H:23]([O:24]C(=O)C2C=CC=CC=2)[C@H:13]1[O:14]C(=O)C1C=CC=CC=1)[CH3:6]>C(O)(=O)C>[CH2:5]([C:7]1[C:8](=[S:47])[NH:9][C:10](=[O:46])[N:11]([CH:45]=1)[C@@H:12]1[O:44][C@H:33]([CH2:34][OH:35])[C@@H:23]([OH:24])[C@H:13]1[OH:14])[CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 18394992HCID 18394992, compound

Product 1

HCID 18394993HCID 18394993, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium hydride (0.1 g) (60% dispersion in mineral oil) was added to dry methanol (50 ml) under an atmosphere of nitrogen at 0° C. The product from step (i) (3.0 g) was added to the above solution and the whole was refluxed for 2 hours. After cooling to room temperature, glacial acetic acid (0.28 ml) was added and the volatiles were then removed under reduced pressure. The residue was dissolved in water (20 ml) and then extracted three times with diethyl ether (20 ml). The aqueous phase was evaporated to dryness under reduced pressure. The resulting solid was triturated with acetone and filtered to leave 5-ethyl-4-thiouridine as a yellow solid (1.39 g).

Workup

  1. temperaturethe whole was refluxed for 2 hours
  2. customthe volatiles were then removed under reduced pressure
  3. dissolutionThe residue was dissolved in water (20 ml)
  4. extractionextracted three times with diethyl ether (20 ml)
  5. customThe aqueous phase was evaporated to dryness under reduced pressure
  6. customThe resulting solid was triturated with acetone
  7. filtrationfiltered

Sources & evidence

ORD record
ord-a5c96c5f4676457ea745dbf64d09e88a
Source dataset
uspto-grants-1999_11
Patent number
US05985849

Reaction notes

Loading…