Sodium Methoxide → HCID 136051363, compound

HRID 2248934Notes

Reaction equation

HRID 2248934 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:45])[C:5]2[S:10][C:9](=[S:11])[N:8]([C@@H:12]3[O:34][C@H:33]([CH2:35][O:36]C(=O)C4C=CC=CC=4)[C@@H:23]([O:24]C(=O)C4C=CC=CC=4)[C@H:13]3[O:14]C(=O)C3C=CC=CC=3)[C:6]=2[N:7]=1.C[O-].[Na+]>CO>[NH2:1][C:2]1[NH:3][C:4](=[O:45])[C:5]2[S:10][C:9](=[S:11])[N:8]([C@@H:12]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:23]([OH:24])[C@H:13]3[OH:14])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 136046889HCID 136046889, compound

Product 1

HCID 136051363HCID 136051363, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 15 (1.25 g, 1.94 mmol) in dry methanol (100 mL) was added sodium methoxide powder until the pH reached 10. The solution was stirred overnight and then neutralized with Dowex H+ resin and filtered. After evaporation of the filtrate, the residue was washed with ether to remove methyl benzoate and the crude material was crystallized from water: yield 520 mg, 81%: mp 220° C. dec.: UV λmax 1H NMR (DMSO-d6) δ 6.48 (d, J=3.00 Hz, 1H, C1,H), 6.99 (s, 2H, NH2), 11.47 (s, 1H, NH), and other sugar protons. Anal. Calcd. for C10H12N4O5S2.H2O: C, z34.28: H, 4.03: N, 15.99: S, 18.30. Found: C, 33.99: H, 3.92: N, 15.68: S, 18.22.

Workup

  1. filtrationfiltered
  2. customAfter evaporation of the filtrate
  3. washthe residue was washed with ether
  4. customto remove methyl benzoate
  5. customthe crude material was crystallized from water

Sources & evidence

ORD record
ord-dd352dbdbc0d4323ac02db9e189bf6bc
Source dataset
uspto-grants-1991_08
Patent number
US05041426

Reaction notes

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