Sodium Methoxide → HCID 178508804, compound

HRID 1638537Notes

Reaction equation

HRID 1638537 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]([C@@H:8]2[O:30][C@H:29]([CH2:31][O:32]C(=O)C3C=CC=CC=3)[C@@H:19]([O:20]C(=O)C3C=CC=CC=3)[C@H:9]2[O:10]C(=O)C2C=CC=CC=2)[C:4]2=[N:41][C:42](=[O:44])[S:43][C:3]=12.C[O-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[CH:6][N:5]([C@@H:8]2[O:30][C@H:29]([CH2:31][OH:32])[C@@H:19]([OH:20])[C@H:9]2[OH:10])[C:4]2=[N:41][C:42](=[O:44])[S:43][C:3]=12

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178508805HCID 178508805, compound

Product 1

HCID 178508804HCID 178508804, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Compound 31 (310 mg, 0.51 mmol) was dissolved in dry methanol (35 mL) and cooled to 5° C. To this solution was added solid sodium methoxide (82 mg, 1.5 mmol) and the solution was stirred at room temperature for 5 h. The mixture was neutralized with Dowex-50 H+ resin, filtered and evaporated to dryness. The residue was triturated with ethyl ether and then recrystallized from aqueous ethanol to yield colorless needles: 120 mg, 80%: mp 132°-134° C.: UV λmax (pH 1) 227 nm (ε17230), 301 (15750): UV λmax (pH 7, 11) 233 nm (ε22300), 305 (19100): 1H NMR (DMSO-d6) δ5.96 (d, J=3.51 Hz, 1H, C1,H), 7.75 (b, 2H, NH2), and other sugar protons. Anal. Calcd. for C10H 12 N4O5S.O.2H2O: C, 35.71: 9.53. Found: C, 35.45: H, 4.88: N, 16.44: S, 9.50.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. customThe residue was triturated with ethyl ether
  4. customrecrystallized from aqueous ethanol
  5. customto yield colorless needles

Sources & evidence

ORD record
ord-d4ccce230c2c4a9c834f327d534dd9df
Source dataset
uspto-grants-1989_11
Patent number
US04880784

Reaction notes

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