Ammonia → Tiazofurin

HRID 1167032Notes

Reaction equation

HRID 1167032 reaction equation
C([O:9][CH2:10][C@H:11]1[O:15][C@@H:14]([C:16]2[S:17][CH:18]=[C:19]([C:21](OCC)=[O:22])[N:20]=2)[C@H:13]([OH:26])[C@@H:12]1[OH:27])(=O)C1C=CC=CC=1.[NH3:28]>C(O)C>[C@@H:14]1([C:16]2[S:17][CH:18]=[C:19]([C:21]([NH2:28])=[O:22])[N:20]=2)[O:15][C@H:11]([CH2:10][OH:9])[C@@H:12]([OH:27])[C@H:13]1[OH:26]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10739325HCID 10739325, compound

Product 1

HCID 457954TiazofurinYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(5′-O-Benzoyl-β-D-ribofuiranosyl)thiazole-4-carboxylate (11, 3.7 g, 942 mmol) was placed in a steel bomb and mixed with freshly prepared cold methanolic ammonia (70 ml, saturated at 0° C. The mixture was protected from moisture and stirred at room temperature for 12 hr. The steel bomb was cooled to 0° C., opened carefully and evaporated to a sticky foam. The residue was triturated with dry toluene (3×50 ml) and the toluene layer was discarded. The residue that obtained was treated with anhydrous ethanol (60 ml) and triturated to give light yellow solid. The solid was filtered, washed with ethyl acetate and dried. The solid was crystallized from ethanol-ethyl acetate to provide 2.25g (90%) of pure product: mp 145-147° C. 1H NMR (DMSO-d6): δ 3.57 (M,2 H), 3.89) (s,2 H), 4.07(m, 1 H), 4.83 (t, 1H), 4.92 (d, 1H), 5.05 (d, 1 H), 5.36 (d, 1 H), 7.56 (s, 1), 7.69 (s, 1) and 8.20 (s,1).

Workup

  1. customsaturated at 0° C
  2. customevaporated to a sticky foam
  3. customThe residue was triturated with dry toluene (3×50 ml)
  4. customThe residue that obtained
  5. customtriturated
  6. customto give light yellow solid
  7. filtrationThe solid was filtered
  8. washwashed with ethyl acetate
  9. customdried
  10. customThe solid was crystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-19f9ec9c5de54587bceda199026f47ca
Source dataset
uspto-grants-2003_09
Patent number
US06613896B1

Reaction notes

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