4-Fluorobenzenesulfonyl chloride → N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-fluoro-benzenesulfonamide

HRID 1716271Notes

Reaction equation

HRID 1716271 reaction equation
[NH2:1][C@@H:2]1[CH2:8][CH:7]=[CH:6][CH2:5][N:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]1=[O:17].[F:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.S(Cl)(Cl)(=O)=O>ClCCl.N1C=CC=CC=1>[CH2:10]([O:9][N:4]1[CH2:5][CH:6]=[CH:7][CH2:8][C@@H:2]([NH:1][S:25]([C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[C:3]1=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 24648Sulfuryl chlorideHCID 68512974HCID 68512974, compound

Product 1

HCID 68516333N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-fluoro-benzenesulfonamideYield 59.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 551 mg of 3-(R)-amino-1-benzyloxy-1,3,4,7-tetrahydro-azepin-2-one from example 1 Step D in 4 mL of dichloromethane and 4 mL of pyridine was added 565 mg of 4-fluorophenyl sulfonyl chloride. The reaction was stirred at room temperature for 24 hours, and an additional 495 mg of the sulfonyl chloride was added. The reaction was stirred for an additional 24 hours, and then the reaction was extracted with ethyl acetate. The mixture was washed with 5% HCl(aq.), NaHCO3(aq.), and NaCl(aq.) solutions. The aqueous layers were re-extracted with ethyl acetate, and the organic layers combined and dried over Na2SO4(s). Filtration and solvent removal gave a light brown solid. Dilution with ethyl ether, filtration, washing of the solids with ethyl ether and drying gave 548 mg of a light brown solid. MS: 391 (M+H).

Workup

  1. stirringThe reaction was stirred for an additional 24 hours
  2. extractionthe reaction was extracted with ethyl acetate
  3. washThe mixture was washed with 5% HCl(aq.), NaHCO3(aq.), and NaCl(aq.) solutions
  4. extractionThe aqueous layers were re-extracted with ethyl acetate
  5. dry with materialdried over Na2SO4(s)
  6. filtrationFiltration and solvent removal
  7. customgave a light brown solid
  8. filtrationDilution with ethyl ether, filtration
  9. washwashing of the solids with ethyl ether
  10. customdrying

Sources & evidence

ORD record
ord-f15abe094f9842a1a040109c8a2ce38a
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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