Salbutamol → HCID 131722754, Verbindung

HRID 1383791

Reaktionsgleichung

Reaktionsgleichung von HRID 1383791
[CH3:1][C:2]([NH:5][CH2:6][CH:7]([OH:17])[C:8]1[CH:9]=[CH:10][C:11]([OH:16])=[C:12]([CH2:14][OH:15])[CH:13]=1)([CH3:4])[CH3:3].[CH3:18][C@@H:19]([C@@H:29]1[C@@:33]2([CH3:49])[C@@H:34]([OH:48])[CH2:35][C@@H:36]3[C@@:41]4([CH3:47])[CH2:42][CH2:43][C@@H:44]([OH:46])[CH2:45][C@H:40]4[CH2:39][CH2:38][C@H:37]3[C@@H:32]2[CH2:31][CH2:30]1)[CH2:20][CH2:21][C:22]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:23].C(OCC)(=O)C>C(O)C>[CH3:4][C:2]([NH:5][CH2:6][CH:7]([OH:17])[C:8]1[CH:9]=[CH:10][C:11]([OH:16])=[C:12]([CH2:14][OH:15])[CH:13]=1)([CH3:1])[CH3:3].[CH3:18][C@@H:19]([C@@H:29]1[C@@:33]2([CH3:49])[C@@H:34]([OH:48])[CH2:35][C@@H:36]3[C@@:41]4([CH3:47])[CH2:42][CH2:43][C@@H:44]([OH:46])[CH2:45][C@H:40]4[CH2:39][CH2:38][C@H:37]3[C@@H:32]2[CH2:31][CH2:30]1)[CH2:20][CH2:21][C:22]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:23]

Komponenten

5

Edukt 3

HCID 2083SalbutamolHCID 8857Ethyl Acetate2×HCID 3035026360-65-6

Produkt 1

HCID 131722754HCID 131722754, VerbindungAusbeute 105,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Salbutamol base (1.2007 g; 5.02 mmol) was dissolved in ethanol (100 mL) with vigorous stirring. Glycodeoxycholic acid (2.4601 g; water content: 4.25% w/w; 5.25 mmol˜5% molar excess) was added and dissolved with stirring. A clear, colourless solution was obtained. The ethanol was removed by vacuum rotary-evaporation to give a viscous, yellow residue. Ethyl acetate (200 mL) was added to the residue and the mixture heated in a water bath with constant agitation. As the yellow residue dissolved, a white precipitate formed. Agitation was continued until the yellow residue disappeared. The ethyl acetate solution was cooled in an ice bath. The precipitate was isolated by vacuum filtration and dried in a vacuum oven at 40° C. for 20 hours to give salbutamol glycodeoxycholate (3.662 g; water content; 4.95% w/w; % yield; 97.9%). Analysis by differential scanning calorimetry from 50 to 200° C. gave no significant thermal event. Slow decomposition was evident after 110° C. A saturated aqueous solution gave a pH of 6.12. The aqueous solubility was greater than 8.35 mg/mL. The theoretical percentage of salbutamol base in the salbutamol glycodeoxycholate 34.74%.

Aufarbeitung

  1. dissolutiondissolved
  2. customA clear, colourless solution was obtained
  3. customThe ethanol was removed by vacuum rotary-evaporation
  4. customto give a viscous, yellow residue
  5. temperaturethe mixture heated in a water bath with constant agitation
  6. dissolutionAs the yellow residue dissolved
  7. customa white precipitate formed
  8. customThe precipitate was isolated by vacuum filtration
  9. customdried in a vacuum oven at 40° C. for 20 hours

Quellen und Nachweise

ORD-Eintrag
ord-2df3eac4f00b4382adc03e49033db230
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255502B1

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