Ethyl Acetate → HCID 68516379, compound

HRID 1716273Notes

Reaction equation

HRID 1716273 reaction equation
[CH2:1]([O:8][N:9]1[CH2:15][CH:14]=[CH:13][CH2:12][C@@H:11]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:10]1=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1.C(OCC)(=O)C>CS(C)=O>[CH2:1]([O:8][N:9]1[CH2:15][CH:14]=[CH:13][CH2:12][C@@H:11]([N:16]([CH2:43][CH2:44][N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)[S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=3)=[CH:22][CH:21]=2)(=[O:18])=[O:19])[C:10]1=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 68512178N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-chloro-phenoxy)-benzenesulfonamide

Product 1

HCID 68516379HCID 68516379, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1.51 g of N-(1-benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-chloro-phenoxy)-benzenesulfonamide from Example 1 Step E in 20 mL of methylsulfoxide (DMSO) was added 2.9 g of Cs2CO3(s) and 1.2 g of 4-(2-chloroethyl)-morpholine hydrochloride. The mixture was heated to 50° C. for 1 hour. The reaction was cooled, and then dissolved with ethyl acetate. The organic layer was washed with NH4Cl(aq) and NaCl(aq) solutions. The aqueous layers were re-extracted with ethyl acetate, and the organic layers were combined and dried over Na2SO4(s). Filtration and solvent removal was followed by column chromatography on silica gel using a hexanes-ethyl acetate gradient. Obtained 1.48 g of a pale brown oil (80% yield). MS: 612 (M+H).

Workup

  1. temperatureThe reaction was cooled
  2. washThe organic layer was washed with NH4Cl(aq) and NaCl(aq) solutions
  3. extractionThe aqueous layers were re-extracted with ethyl acetate
  4. dry with materialdried over Na2SO4(s)
  5. filtrationFiltration and solvent removal

Sources & evidence

ORD record
ord-3ec86b8a43e0468e9a80c9f13be4dc59
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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