Hydrochloric Acid → 7-(beta-Galactosyl)-4-methylcoumarin-3-acetic acid

HRID 1080606Notes

Reaction equation

HRID 1080606 reaction equation
C([C@:4]1([OH:41])[C@@H:9]([CH2:10][OH:11])[O:8][C@:7](C(=O)C)([C:12]2[CH:21]=[C:20]3[C:15]([C:16]([CH3:29])=[C:17]([CH2:23][C:24]([O:26]CC)=[O:25])[C:18](=[O:22])[O:19]3)=[CH:14][CH:13]=2)[C@:6](C(=O)C)([OH:33])[C@@:5]1(C(=O)C)[OH:37])(=O)C.[OH-].[K+].Cl>CO>[C@@H:7]1([C:12]2[CH:21]=[C:20]3[C:15]([C:16]([CH3:29])=[C:17]([CH2:23][C:24]([OH:26])=[O:25])[C:18](=[O:22])[O:19]3)=[CH:14][CH:13]=2)[O:8][C@H:9]([CH2:10][OH:11])[C@H:4]([OH:41])[C@H:5]([OH:37])[C@H:6]1[OH:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 131717828HCID 131717828, compound

Product 1

HCID 186507157-(beta-Galactosyl)-4-methylcoumarin-3-acetic acidYield 60.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 7-(tetraacetyl-β-galactosyl)-4-methylcoumarin-3-acetic acid, ethyl ester (3) (422 mg, 0.712 mmol) in methanol was added 6.8M KOH (5 mL) and the solution was stirred overnight at room temperature. The solution was neutralized by the addition of 1N HCl and evaporated to dryness under reduced pressure. The residue was dissolved in water (10 mL) and desalted using C18Sep Pack Cartridges in 10×1 mL portions. The C18Sep Pack Cartridge (Waters Part No. 65910) was washed with methanol (3 mL) and water (3 mL) before the sample was applied in 1 mL. The cartridge was then washed with water (3 mL) to remove any salt followed by metahnol (3 mL) which eluted the desired product as determined by TLC (silica gel, acetone:20 mM NaOAc 9:1). The methanol washes were pooled and evaporated under reduced pressure and the while solid obtained was recrystallized from ethanol/water to give 170 mg (0.43 mmol, 60%) of 4 as white crystals: m.p. 186°-188° C.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in water (10 mL)
  3. washThe C18Sep Pack Cartridge (Waters Part No. 65910) was washed with methanol (3 mL) and water (3 mL) before the sample
  4. washThe cartridge was then washed with water (3 mL)
  5. customto remove any salt
  6. washeluted the desired product
  7. customevaporated under reduced pressure
  8. customthe while solid obtained
  9. customwas recrystallized from ethanol/water

Sources & evidence

ORD record
ord-fea090d6c13a4113822b70f04cf62ab7
Source dataset
uspto-grants-1996_12
Patent number
US05583001

Reaction notes

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