Glycopyrrolate → (1,1-Dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate;4-methylbenzenesulfonate

HRID 1042960

Reaktionsgleichung

Reaktionsgleichung von HRID 1042960
[CH3:1][N+:2]1([CH3:23])[CH2:6][CH:5]([O:7][C:8]([C:10]([OH:22])([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:9])[CH2:4][CH2:3]1.[Br-].[S:25]([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)([O-:28])(=[O:27])=[O:26].[Ag+]>O>[CH3:1][N+:2]1([CH3:23])[CH2:6][CH:5]([O:7][C:8]([C:10]([OH:22])([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:9])[CH2:4][CH2:3]1.[S:25]([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)([O-:28])(=[O:27])=[O:26]

Komponenten

4

Edukt 2

HCID 11693GlycopyrrolateHCID 85606Benzenesulfonic acid, 4-methyl-, silver(1+) salt (1:1)

Produkt 1

HCID 23726018(1,1-Dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate;4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

In a dark room, silver tosylate (3.5 g) was dissolved in water (˜100 mL) by sonication. The solution was heated to approximately 40° C. and additional water was added (˜15 mL). An equimolar amount of glycopyrrolate bromide (5 g) (mixture of R,S and S,R diastereomers) was added and immediately resulted in a yellow precipitate. The slurry was stirred at approximately 40° C. overnight, and then slowly cooled while stirring to ambient temperature. At ambient temperature, the solids were vacuum filtered and the wet cake was washed three times with approximately 10 mL of water. The mother liquor was collected and filtered two times through a 0.2 μm nylon filter with glass microfiber (GMF). A clear solution was observed after filtration and was lyophilized at approximately −50° C. After 6 days, a mixture of white, needle-like and slightly sticky, glassy solids was observed. Toluene (−20 mL) was added, and the slurry was briefly sonicated and then stirred at ambient temperature. Additional toluene (˜80 mL) was added for easier stirring, and the mixture was allowed to stand at ambient conditions for 1 day. Solids of glycopyrrolate tosylate were collected by vacuum filtration and vacuum drying at ambient temperature for 1 day.

Aufarbeitung

  1. customimmediately resulted in a yellow precipitate
  2. temperatureslowly cooled
  3. stirringwhile stirring to ambient temperature
  4. customAt ambient temperature
  5. filtrationfiltered
  6. washthe wet cake was washed three times with approximately 10 mL of water
  7. customThe mother liquor was collected
  8. filtrationfiltered two times through a 0.2 μm nylon
  9. filtrationfilter with glass microfiber (GMF)
  10. filtrationafter filtration
  11. customwas lyophilized at approximately −50° C
  12. waitAfter 6 days
  13. additiona mixture of white, needle-like
  14. additionToluene (−20 mL) was added
  15. customthe slurry was briefly sonicated
  16. stirringstirred at ambient temperature
  17. additionAdditional toluene (˜80 mL) was added
  18. stirringfor easier stirring
  19. waitto stand at ambient conditions for 1 day
  20. filtrationSolids of glycopyrrolate tosylate were collected by vacuum filtration and vacuum
  21. customdrying at ambient temperature for 1 day

Quellen und Nachweise

ORD-Eintrag
ord-825ba4203c424464bb507cf3496c71b3
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08558008B2

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