Cesium carbonate → [(6R,7S)-2-fluoro-6-methyl-8-oxo-9-(2,2,2-trifluoro-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester

HRID 1348651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1348651
[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:11]=2[O:10][C@@H:9]1[CH3:21])([CH3:4])([CH3:3])[CH3:2].O([CH2:31][C:32]([F:35])([F:34])[F:33])S(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:31][C:32]([F:35])([F:34])[F:33])[C:12]2[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:11]=2[O:10][C@@H:9]1[CH3:21])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 67076781tert-Butyl ((2R,3S)-7-fluoro-2-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamate

Produkt 1

HCID 67077130[(6R,7S)-2-fluoro-6-methyl-8-oxo-9-(2,2,2-trifluoro-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl esterAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3.00 g (10.0 mmol) ((6R,7S)-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester and 3.37 g (15.0 mmol) 2,2,2-trifluoroethyl triflate in 30 ml dimethylformamide were treated with 4.73 g (15.0 mmol) cesium carbonate for 6 hours. The solvent was distilled off at low pressure and the residue was extracted with water/ethylacetate. Chromatography on silicagel with heptane/ethylacetate 100:0 to 0:100 yielded 3.79 g (99%) [(6R,7S)-2-fluoro-6-methyl-8-oxo-9-(2,2,2-trifluoro-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester, MS m/e (%): 393.3 (M+H+, 100).

Aufarbeitung

  1. distillationThe solvent was distilled off at low pressure
  2. extractionthe residue was extracted with water/ethylacetate

Quellen und Nachweise

ORD-Eintrag
ord-909bc0d6c56e45b895dd0e8330050394
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211573B2

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