Sodium Methoxide → HCID 21825583, compound

HRID 917829Notes

Reaction equation

HRID 917829 reaction equation
C[O-].[Na+].C([O:7][C@@H:8]1[C@H:12]([O:13]C(=O)C)[C@@H:11]([CH2:17][O:18]C(=O)C)[O:10][C@H:9]1[N:22]1[N:26]=[C:25]([C:27](=[S:29])[NH2:28])[CH:24]=[N:23]1)(=O)C>CO>[C@@H:9]1([N:22]2[N:26]=[C:25]([C:27](=[S:29])[NH2:28])[CH:24]=[N:23]2)[O:10][C@H:11]([CH2:17][OH:18])[C@@H:12]([OH:13])[C@H:8]1[OH:7]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 21825599HCID 21825599, compound

Product 1

HCID 21825583HCID 21825583, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide in methanol (60 mg of sodium in 30 ml of methanol) was added to 1.0 g of 9 and the resulting solution was stirred at room temperature for 4 hr. After neutralization with Amberlite IRC 50, the solution was filtered, and the filtrate was evaporated to dryness. Methanol and silica gel (2.5 g) were added to the syrup, and the mixture was evaporated to dryness. The silica gel mixture was added to a dry-packed silica gel column (1 × 18 cm) and the column was eluted with chloroform (0.1 liter), ethylacetate-chloroform (1:1, 0.1 liter) and ethyl acetate (0.4 liter); 20 ml fractions were collected. Fractions 14-28 provided 0.61 g (91%) of 11 as a syrup: nmr (DMSO-d6) δ 5.95 (d, 1, J1',2' 4.0 Hz, 1'--H), 8.32 (s, 1, 5--H).

Workup

  1. filtrationAfter neutralization with Amberlite IRC 50, the solution was filtered
  2. customthe filtrate was evaporated to dryness
  3. additionMethanol and silica gel (2.5 g) were added to the syrup
  4. customthe mixture was evaporated to dryness
  5. additionThe silica gel mixture was added to a dry-packed silica gel column (1 × 18 cm)
  6. washthe column was eluted with chloroform (0.1 liter), ethylacetate-chloroform (1:1, 0.1 liter) and ethyl acetate (0.4 liter)
  7. custom20 ml fractions were collected

Sources & evidence

ORD record
ord-cefe3f2f709d49339705b52d18a1c9a3
Source dataset
uspto-grants-1976_07
Patent number
US03968103

Reaction notes

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