Hydrochloric Acid → HCID 131727135, Verbindung

HRID 709331

Reaktionsgleichung

[CH3:1][C@H:2]1[C@:19]([OH:24])([C:20]([CH2:22][OH:23])=[O:21])[C@:18]2([CH3:25])[C@H:4]([C@H:5]3[C@:15]([F:27])([C@@H:16]([OH:26])[CH2:17]2)[C@:14]2([CH3:28])[C:8](=[CH:9][C:10]([CH:12]=[CH:13]2)=[O:11])[CH2:7][CH2:6]3)[CH2:3]1.[CH3:29][S:30](Cl)(=[O:32])=[O:31].Cl>N1C=CC=CC=1>[CH3:1][C@H:2]1[C@:19]([OH:24])([C:20]([CH2:22][OH:23])=[O:21])[C@:18]2([CH3:25])[C@H:4]([C@H:5]3[C@:15]([F:27])([C@@H:16]([OH:26])[CH2:17]2)[C@:14]2([CH3:28])[C:8](=[CH:9][C:10]([CH:12]=[CH:13]2)=[O:11])[CH2:7][CH2:6]3)[CH2:3]1.[S:30]([O-:32])(=[O:11])(=[O:31])[CH3:29]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A 200 mL Erlenmeyer flask equipped with a magnetic stir bar and a rubber septum was charged with 5 grams of dexamethasone (12.7 mmol, 1 equivalent) and 16 mL of anhydrous pyridine. The flask was cooled to 0° C. with an ice bath, and 1.2 mL of methanesulfonyl chloride was added. After 1 hour, 0.8 mL of additional methanesulfonyl chloride was added. At two hours, the solution was poured into 100 mL of cold 1M HCl, forming a precipitate. The precipitate was filtered and redissolved in 250 mL of ethanol, and precipitated into 250 mL of 1M HCl. The precipitate was filtered and recrystallized in ethanol, filtered, and dried under vacuum yielding 4.95 g (82.6%) of dexamethasone mesylate.

Aufarbeitung

customA 200 mL Erlenmeyer flask equipped with a magnetic stir bar
waitAt two hours
customforming a precipitate
filtrationThe precipitate was filtered
dissolutionredissolved in 250 mL of ethanol
customprecipitated into 250 mL of 1M HCl
filtrationThe precipitate was filtered
customrecrystallized in ethanol
filtrationfiltered
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-9fb198e288bb401dac4792f81b965445
Quelldatensatz: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09180132B2

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