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

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2,2,2-Trifluoroethyl trifluoromethanesulfonate	HCID 80366	—
Reactant	tert-Butyl ((2R,3S)-7-fluoro-2-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamate	HCID 67076781	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[(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	HCID 67077130	87.1%

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07211573B2
Source dataset	uspto-grants-2007_05
ORD ID	ord-dcb907fcc3604a5dafdbbced597b3de6
Source note	uspto-grants-2007_05