Reaktionsgleichung
[C:1]([C@@H:3]1[CH2:8][C@H:7]2[C@H:5]([CH2:6]2)[N:4]1[C:9](=[O:33])[C@@H:10]([NH:22]C(=O)OCC1C=CC=CC=1)[C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][C:13]([OH:21])([CH2:14]3)[CH2:12]1)[CH2:18]2)#[N:2]>C(#N)C.[Pd]>[CH2:8]1[C@@H:3]([C:1]#[N:2])[N:4]([C:9]([C@@H:10]([NH2:22])[C:11]23[CH2:12][C:13]4([OH:21])[CH2:19][CH:17]([CH2:16][CH:15]([CH2:14]4)[CH2:20]2)[CH2:18]3)=[O:33])[C@@H:5]2[C@H:7]1[CH2:6]2Komponenten
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of benzyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxo-ethyl]carbamate (10 gm) of formula-IX in acetonitrile, 5% Pd/C (50% wet, 1 gm) was added. Hydrogen gas was bubbled through the reaction mass for 4 hrs at 20-25° C. After complete conversion of starting material, the reaction mass was filtered. The filtrate was evaporated to yield SAXAGLIPTIN free base of formula-I as a foamy solid. To the solid ethyl acetate (5 ml), 20 micro liters of water and n-hexane (20 ml) were added, the mixture stirred at 0-5° C. and the white solid formed was filtered to yield 7.06 gm (95%) of SAXAGLIPTIN MONO HYDRATE of formula-XII. The solid obtained was dissolved in ethyl acetate (30 ml), 2.15 ml of concentrated hydrochloric acid added at 20-25° C., stirred for one hour and the white solid formed was filtered to yield saxagliptin dihydrate mono-hydrochloride of formula-II.
Aufarbeitung
- customHydrogen gas was bubbled through the reaction mass for 4 hrs at 20-25° C
- filtrationAfter complete conversion of starting material, the reaction mass was filtered
- customThe filtrate was evaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-2100f039bdb9423c9d19dca764e87e57
- Quelldatensatz
- uspto-grants-2014_03
- Patentnummer
- US08664443B2
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