Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Lansoprazole | HCID 3883 | — |
| Edukt | Hexane | HCID 8058 | — |
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Isopropanol hexane | HCID 21585144 | — |
| Lösungsmittel | Isopropanol | HCID 3776 | — |
| Produkt | Dexlansoprazole | HCID 9578005 | 27,2% |
Reaktionsschritte
Lansoprazole (racemate) (34.2 g) was dissolved in 2-propanol (1,710 ml) and hexane (1,140 ml) containing triethylamine (0.2%) and fractionated by HPLC (column: CHIRALCEL OD 50 mm dia.×500 mm, temperature: room temperature, mobile phase: hexane/2-propanol=85/15, flow rate: 60 ml/min, detection wavelength: 285 nm, 1 shot: about 300 mg) to isolate the individual optical isomers. Fractions of an optical isomer of shorter retention time were combined and concentrated; the individual lots were combined and dissolved in ethanol (250 ml); after triethylamine (3 ml) was added, the solution was filtered through a 0.45 μm filter. After the filtrate was concentrated, hexane was added, and the filtrate was again evaporated to dryness to yield R(+)-lansoprazole (9.31 g, optical purity 98.3% ee) as an amorphous substance.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07737282B2 |
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| Quelldatensatz | uspto-grants-2010_06 |
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| ORD ID | ord-8a05a436f6a74f90915a0150f499cd3e |
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| Quellennotiz | uspto-grants-2010_06 |
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