Cesium carbonate → (6R,7S)-7-dibenzylamino-6-ethyl-2-fluoro-9-(2,2,2-trifluoro-ethyl)-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one

HRID 1348663Notes

Reaction equation

HRID 1348663 reaction equation
[CH2:1]([N:8]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@@H:9]1[C:15](=[O:16])[NH:14][C:13]2[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:12]=2[O:11][C@@H:10]1[CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O([CH2:39][C:40]([F:43])([F:42])[F:41])S(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:24]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]1[C:15](=[O:16])[N:14]([CH2:39][C:40]([F:43])([F:42])[F:41])[C:13]2[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:12]=2[O:11][C@@H:10]1[CH2:22][CH3:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 21091451(-)-(6R,7S)-7-dibenzylamino-6-ethyl-2-fluoro-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one

Product 1

HCID 21091452(6R,7S)-7-dibenzylamino-6-ethyl-2-fluoro-9-(2,2,2-trifluoro-ethyl)-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-oneYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.50 g (1.24 mmol) (−)-(6R,7S)-7-dibenzylamino-6-ethyl-2-fluoro-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one and 0.44 g (1.85 mmol) 2,2,2-trifluoroethyl triflate in 5 ml dimethylformamide were treated with 0.61 g (1.85 mmol) cesium carbonate for 18 hours. The mixture was extracted with water/ethylacetate. Chromatography on silicagel with heptane/ethylacetate 70:30 yielded 0.34 g (57%) (6R,7S)-7-dibenzylamino-6-ethyl-2-fluoro-9-(2,2,2-trifluoro-ethyl)-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one, MS m/e (%): 487.4 (M+H+, 100).

Workup

  1. extractionThe mixture was extracted with water/ethylacetate

Sources & evidence

ORD record
ord-7da0a05783ab4273a4394f911dd1a27a
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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