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 1348600Notes

Reaction equation

HRID 1348600 reaction equation
[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]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 67076781(6R,7S)-7-(Boc-amino)-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-azabenzocyclohepten

Product 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 esterYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.50 g (1.61 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 in 5 ml dimethylformamide were added at room temperature 0.57 g (2.42 mmol) 2,2,2-trifluorethyl triflate and 0.80 g (2.43 mmol) cesium carbonate. Stirring was continued for 5 hours. Extraction with ethylacetate/water and chromatography on silicagel with heptane to ethylacetate/heptane 2:8 yielded 0.55 g (87%) [(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 (%): 415.3 (M+Na+, 100), 393.2 (M+H+, 8), 293.1 (43).

Workup

  1. extractionExtraction with ethylacetate/water and chromatography on silicagel with heptane to ethylacetate/heptane 2:8

Sources & evidence

ORD record
ord-dcb907fcc3604a5dafdbbced597b3de6
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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