Cesium carbonate → 3-(4-Fluoro-benzenesulfonyl)-1-trityloxy-azepan-2-one

HRID 1716321Notes

Reaction equation

HRID 1716321 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]([O:20][C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:7](=[O:19])[CH2:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[F:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([CH:8]2[CH2:2][CH2:3][CH2:4][CH2:5][N:6]([O:20][C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:7]2=[O:19])(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 86619941N-(4-Bromo-butyl)-2-(4-fluoro-benzenesulfonyl)-N-trityloxy-acetamide

Product 1

HCID 685136933-(4-Fluoro-benzenesulfonyl)-1-trityloxy-azepan-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4-Bromo-butyl)-2-(4-fluoro-benzenesulfonyl)-N-trityloxy-acetamide prepared from step E (170.2 mg, 0.279 mmol) and Cs2CO3 (187.3 mg, 0.575 mmol) in anhydrous DMF (6 mL) was stirred at room temperature for overnight.). The reaction mixture was diluted with EtOAc and washed sequentially with water and saturated NaCl solution. The organic phase was then dried over anhydrous Na2SO4 and concentrated under reduced pressure to gave a crude material, which was then purified by a column chromatography (0˜30% EtOAc in hexane). MS: 552.2 (M+Na)+.

Workup

  1. washwashed sequentially with water and saturated NaCl solution
  2. dry with materialThe organic phase was then dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-538f2771775c4235847da2d0a58d9187
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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