HCID 13827068, compound → HCID 6712996, compound

HRID 377153Notes

Reaction equation

HRID 377153 reaction equation
C([O:9][C@@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@H:11]1[N:34]1[CH:41]=[C:40]([F:42])[C:38](=[O:39])[NH:37][C:35]1=[O:36])(=O)C1C=CC=CC=1>CO.C[O-].[Na+]>[C@@H:11]1([N:34]2[CH:41]=[C:40]([F:42])[C:38](=[O:39])[NH:37][C:35]2=[O:36])[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@H:10]1[OH:9]

Participants

4

Reactant 1

HCID 13827068HCID 13827068, compound

Product 1

HCID 6712996HCID 6712996, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

To a solution of compound 3 (11.7 g, 20.37 mmol) in MeOH (300 ml), NaOMe (4.2 ml of a methanolic 25% w/v solution) was added and the solution was stirred until the reaction was complete. The solvent was then evaporated and the residue was dissolved in H2O (200 ml), washed with ether and neutralized with Dowex 50 ion exchange resin. After filtration of the resin, the aqueous solution was evaporated to give compound 4 (4.92 g, 92% yield) as a white foam.

Workup

  1. additionwas added
  2. customThe solvent was then evaporated
  3. dissolutionthe residue was dissolved in H2O (200 ml)
  4. washwashed with ether and neutralized with Dowex 50 ion exchange resin
  5. filtrationAfter filtration of the resin
  6. customthe aqueous solution was evaporated

Sources & evidence

ORD record
ord-870f76ebc2e24616baa0e567ad067f8a
Source dataset
uspto-grants-2000_02
Patent number
US06025335

Reaction notes

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