Cesium carbonate → 1-((4S,5R)-5-(4-(6-(2-oxa-5-azaspiro[3.4]octan-5-ylmethyl)pyridin-3-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-3-yl)-2,2-difluoroethanone
Reaktionsgleichung
[CH2:1]1[C:4]2([CH2:8][CH2:7][CH2:6][NH:5]2)[CH2:3][O:2]1.Cl[CH2:10][C:11]1[N:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C@H:23]3[O:27][C:26]([CH3:29])([CH3:28])[N:25]([C:30](=[O:34])[CH:31]([F:33])[F:32])[C@@H:24]3[CH2:35][F:36])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:3]1[C:4]2([CH2:8][CH2:7][CH2:6][N:5]2[CH2:10][C:11]2[N:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C@H:23]4[O:27][C:26]([CH3:29])([CH3:28])[N:25]([C:30](=[O:34])[CH:31]([F:33])[F:32])[C@@H:24]4[CH2:35][F:36])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:1][O:2]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 55 °C
Versuchsvorschrift
A mixture of 2-oxa-5-azaspiro[3.4]octane (0.1 mmol, 15.8 mg), 1-{(4S,5R)-5-[4-(6-Chloromethyl-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl}-2,2-difluoro-ethanone (Example 99, Step 2, 0.09 mmol, 37 mg) and cesium carbonate (0.25 mmol, 81 mg) and acetonitrile (1 mL) was heated to 55° C. for 5 hours. The crude mixture was filtered on a bed of celite and the cake was washed with CH2Cl2 (2 mL). The volatiles were removed. The crude mixtures were used “as is” in step 2.
Aufarbeitung
- filtrationThe crude mixture was filtered on a bed of celite
- washthe cake was washed with CH2Cl2 (2 mL)
- customThe volatiles were removed
Quellen und Nachweise
- ORD-Eintrag
- ord-a30bdc08456846fea704aae2608f7074
- Quelldatensatz
- uspto-grants-2015_07
- Patentnummer
- US09073894B2
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