Sodium → HCID 21853339, compound

HRID 838873Notes

Reaction equation

HRID 838873 reaction equation
C([NH:4][C:5]1[S:9][N:8]([C@@H:10]2[O:22][C@H:21]([CH2:23][O:24]C(=O)C)[C@@H:16]([O:17]C(=O)C)[C@H:11]2[O:12]C(=O)C)[C:7](=[O:28])[N:6]=1)(=O)C.C(NC1SN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N=1)(=O)C.[Na]>CO>[NH2:4][C:5]1[S:9][N:8]([C@@H:10]2[O:22][C@H:21]([CH2:23][OH:24])[C@@H:16]([OH:17])[C@H:11]2[OH:12])[C:7](=[O:28])[N:6]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 21853337HCID 21853337, compoundHCID 21853340HCID 21853340, compound

Product 1

HCID 21853339HCID 21853339, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 5-acetamido-2-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-thiadiazol-3-one (4,1.0 g) or 5-acetamido-2-(β-D-ribofuranosyl)-1,2,4-thiadiazol-3-one (7) in anhydrous methanol (50 ml) was added 1N sodium methozide in methanol, till the pH of the solution was 9.0 and the solution was stirred at 30° for several days. After the reaction was complete, the solution was neutralized by stirring for 15 min with Amberlite IRC-50 (H+) resin. The resin was filtered off and the filtrate was evaporated to dryness in vacuo. The residue was chromatographed on a silica gel column (2.5 × 45 cms) using ethylacetate:water:n-propanol (4:2:1), v/v, upper phase). The appropriate fractions were pooled, solvent evaporated and the reisdue crystallized from aaueous ethanol to yield 0.24 g (40.2%), m.p. > 240° (dec.); 1H nmr (Me2SO-d6) δ5.63 (d, J=4.5 Hz, C1'H); uv λmax (pH 1) 220 nm (ε 14,950), 273 (5000); λmax (pH 7) 220 nm (ε 13,950), 255 (6250); λmax (pH 11) 230 nm (ε 1,200), 278 sh (7500).

Workup

  1. stirringby stirring for 15 min with Amberlite IRC-50 (H+) resin
  2. filtrationThe resin was filtered off
  3. customthe filtrate was evaporated to dryness in vacuo
  4. customThe residue was chromatographed on a silica gel column (2.5 × 45 cms)
  5. customsolvent evaporated
  6. customthe reisdue crystallized from aaueous ethanol
  7. customto yield 0.24 g (40.2%), m.p. > 240° (dec.)

Sources & evidence

ORD record
ord-e30a25fe3fbd460d8aa4f407417d218f
Source dataset
uspto-grants-1978_06
Patent number
US04093624

Reaction notes

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