Water → 7-beta-Galactosylcoumarin-3-carboxylic acid

HRID 1065935

Reaktionsgleichung

Reaktionsgleichung von HRID 1065935
[OH-].[K+].O.[C@@H:4]1([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[C:20]([C:26]([O:28]CC)=[O:27])[C:21](=[O:25])[O:22]3)=[CH:17][CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]>CO>[C@@H:4]1([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[C:20]([C:26]([OH:28])=[O:27])[C:21](=[O:25])[O:22]3)=[CH:17][CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]

Komponenten

5

Edukt 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 22809745Ethyl 7-beta-galactosylcoumarin-3-carboxylate

Produkt 1

HCID 228097447-beta-Galactosylcoumarin-3-carboxylic acidAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 24 g of potassium hydroxide, 80 ml of water, 240 ml of methanol, and 20 g (0.035 mol) of ethyl 7-β-galactosylcoumarin-3-carboxylate [Burd et al, Clin. Chem. 23, 1402 (1977)] was stirred at 50° C. for 15 hours. When cool, the methanol was removed under reduced pressure. The concentrated aqueous solution was acidified to pH 2 with concentrated hydrochloric acid. The precipitate was collected, washed with cold water, and recrystallized from hot water. The crystals were collected, washed with acetone, and dried at 80° C. for 1 hr. This gave 12 g (54% yield) of 7-β-galactosylcoumarin-3-carboxylic acid as white crystals, mp 250°-255° C.

Aufarbeitung

  1. temperatureWhen cool
  2. customthe methanol was removed under reduced pressure
  3. customThe precipitate was collected
  4. washwashed with cold water
  5. customrecrystallized from hot water
  6. customThe crystals were collected
  7. washwashed with acetone
  8. customdried at 80° C. for 1 hr

Quellen und Nachweise

ORD-Eintrag
ord-fc38d6d3c1424bd4a66a2a6ffbe72d82
Quelldatensatz
uspto-grants-1982_05
Patentnummer
US04331590

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