Sodium Methoxide → HCID 21825584, compound

HRID 917830Notes

Reaction equation

HRID 917830 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[CH:23]=[C:22]([C:24](=[S:26])[NH2:25])[N:21]=[N:20]1)(=O)C.C[O-].[Na+]>CO>[C@@H:6]1([N:19]2[CH:23]=[C:22]([C:24](=[S:26])[NH2:25])[N:21]=[N:20]2)[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 21825582HCID 21825582, compound

Product 1

HCID 21825584HCID 21825584, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2,3,5-Tri-O-acetyl-β -D-ribofuranosyl)-1,2,3-triazole-4-thiocarboxamide (1.0 g) was added to sodium methoxide in methanol (60 mg of sodium in 30 ml of methanol) and the resulting solution was stirred at room temperature for 4 hr. After neutralization of the solution with Amberlite IRC 50, the solution was filtered, and the filtrate was evaporated to dryness. The product was crystallized from ethanol to give 0.55 g (82%) of 12: m.p. 152°-154°; [α]D25 -85.2° (c 1.00, water); nmr (DMSO-d6) δ 6.04 (d, 1, J1',2' 4.8 Hz, 1'--H), 8.90 (s, 1, 5--H).

Workup

  1. filtrationAfter neutralization of the solution with Amberlite IRC 50, the solution was filtered
  2. customthe filtrate was evaporated to dryness
  3. customThe product was crystallized from ethanol

Sources & evidence

ORD record
ord-dc687b275ec547a59c5a4f9a64ffe32a
Source dataset
uspto-grants-1976_07
Patent number
US03968103

Reaction notes

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