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

HRID 2683노트

반응식

HRID 2683 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2e05a904ddd240dbb2ba875f082acfe9
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731158

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