Dorzolamide → HCID 86635737, Verbindung

HRID 1928583

Reaktionsgleichung

Reaktionsgleichung von HRID 1928583
[CH3:1][CH2:2][NH:3][C@@H:4]1[C:11]2[CH:12]=[C:13]([S:15]([NH2:18])(=[O:17])=[O:16])[S:14][C:10]=2[S:7](=[O:9])(=[O:8])[C@@H:6]([CH3:19])[CH2:5]1.C1(C)C=CC(C([C@@:28]([C:44]([OH:46])=[O:45])([OH:43])[C@@:29](C(C2C=CC(C)=CC=2)=O)([OH:33])[C:30]([OH:32])=[O:31])=O)=CC=1>CC(O)C>[CH3:1][CH2:2][NH:3][C@@H:4]1[C:11]2[CH:12]=[C:13]([S:15]([NH2:18])(=[O:17])=[O:16])[S:14][C:10]=2[S:7](=[O:8])(=[O:9])[C@@H:6]([CH3:19])[CH2:5]1.[C:30]([CH:29]([CH:28]([C:44]([O-:46])=[O:45])[OH:43])[OH:33])([O-:32])=[O:31]

Komponenten

4

Edukt 2

HCID 5284549DorzolamideHCID 29414711Di-para-toluoyl-L-tartaric acid

Produkt 1

HCID 86635737HCID 86635737, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Dorzolamide trans racemate of formula (II) (0.8 g) and (−)-di-p-toluoyl-L-tartaric acid (0.22 g) were dissolved in refluxing 2-propanol (45 mL). The so obtained solution was distilled at normal pressure up to a final volume of 20 mL. The resulting suspension was stirred at refluxing temperature further 2 hours and then cooled to 20° C. over 7 hours. The solid was isolated by vacuum filtration washing with 2-propanol (4 mL) and then dried in vacuum oven at 40° C. to give Dorzolamide tartrate (1st crop) (0.626 g). This compound (0.601 g) was dissolved in refluxing 2-propanol and the solution was distilled at normal pressure up to a final volume of 18 mL. The resulting suspension was cooled to 20° C. over 7 hours. The solid was isolated by vacuum filtration washing with 2-propanol (4 mL) and then dried in vacuum oven at 40° C. to give Dorzolamide tartrate (2nd crop) (0.49 g). This compound was submitted to a further re-crystallization following the latter procedure (the solution was distilled at normal pressure up to a final volume of 15 mL). The resulting solid was isolated by vacuum filtration then dried in vacuum oven at 50° C. to give the title compound (0.379 g; 85-87% e.e.) as a white solid.

Aufarbeitung

  1. customThe so obtained solution
  2. distillationwas distilled at normal pressure up to a final volume of 20 mL
  3. temperatureat refluxing temperature further 2 hours
  4. customThe solid was isolated by vacuum filtration
  5. washwashing with 2-propanol (4 mL)
  6. customdried in vacuum oven at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-0954d739392f411e90f15d55655c95b5
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183391B2

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