Sodium Methoxide → HCID 54499710, compound

HRID 1424323Notes

Reaction equation

HRID 1424323 reaction equation
C([O:4][C@H:5]1[C@H:17]([O:18]C(=O)C)[C@H:16]([O:22]C(=O)C)[C@H:15]([CH3:26])[O:14][C@@H:6]1[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)C.C[O-].[Na+]>CO>[S:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C@H:6]1[O:14][C@@H:15]([CH3:26])[C@@H:16]([OH:22])[C@@H:17]([OH:18])[C@@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 14131728HCID 14131728, compound

Product 1

HCID 54499710HCID 54499710, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Compound of example 8 (224 g) is dissolved in methanol (500 ml) and NaOMe (2 g, 37 mmol) is added. The reaction mixture is stirred at 40° C. for 21/2 h. Methanol (250 ml) is distilled off and CO2 is bubbled through the remaining solution for 5 min reaching pH=7. The reaction mixture is evaporated and isobutyl acetate (450 ml) is added. 50 ml of solvent is evaporated and the resulting mixture is subjected to crystallization by letting it at room temperature for 24 h. The white crystalline solid formed is filtered and washed with tert-butyl methyl ether (200 ml) giving 110 g (73%) of product after drying.

Workup

  1. distillationMethanol (250 ml) is distilled off
  2. customCO2 is bubbled through the remaining solution for 5 min
  3. customThe reaction mixture is evaporated
  4. additionisobutyl acetate (450 ml) is added
  5. custom50 ml of solvent is evaporated
  6. customthe resulting mixture is subjected to crystallization
  7. customat room temperature
  8. customfor 24 h
  9. customThe white crystalline solid formed
  10. filtrationis filtered
  11. washwashed with tert-butyl methyl ether (200 ml)

Sources & evidence

ORD record
ord-d51f53cad16b4e3ca1c6cce3c2097664
Source dataset
uspto-grants-2015_01
Patent number
US08927698B2

Reaction notes

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