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

HRID 536602

반응식

HRID 536602 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2b882e321c2e4912bada6dee71995f52
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859610B2

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