4-(4-Chlorophenoxy)benzene-1-sulfonyl chloride → N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-chloro-phenoxy)-benzenesulfonamide

HRID 1716269Notes

Reaction equation

HRID 1716269 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].[Cl:18][C:19]1[CH:35]=[CH:34][C:22]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[CH:21][CH:20]=1>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:30]([C:27]2[CH:28]=[CH:29][C:24]([O:23][C:22]3[CH:34]=[CH:35][C:19]([Cl:18])=[CH:20][CH:21]=3)=[CH:25][CH:26]=2)(=[O:31])=[O:32])[C:3]1=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 27577504-(4-Chlorophenoxy)benzene-1-sulfonyl chlorideHCID 68512974HCID 68512974, compound

Product 1

HCID 68512178N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-chloro-phenoxy)-benzenesulfonamideYield 57.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3.69 g of 3-(R)-amino-1-benzyloxy-1,3,4,7-tetrahydro-azepin-2-one from Step D in 30 mL of pyridine was added 6.28 g of 4-(4-chloro-phenoxy)-benzene sulfonyl chloride. The reaction was stirred at room temperature for 5 days. The reaction was extracted with ethyl acetate, and washed with 5% HCl (aq.) twice, NaHCO3 (aq.) twice, and NaCl (aq.) once. The aqueous layers were re-extracted with ethyl acetate, and the organic layers combined and dried over Na2SO4(s). The reaction mixture was filtered and the solvent removed. The mixture was dissolved in dichloromethane, and filtered over silica gel. The dichloromethane layer was discarded. The silica gel was eluted with ethyl acetate, and the solvent removed under vacuum. Next, ethyl ether was added, and the solids collected under vacuum. The solids were washed with ethyl ether, and dried. Obtained 4.59 g of a white solid. MS: 521 (M+Na), 499 (M+H).

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. washwashed with 5% HCl (aq.) twice
  3. extractionThe aqueous layers were re-extracted with ethyl acetate
  4. dry with materialdried over Na2SO4(s)
  5. filtrationThe reaction mixture was filtered
  6. customthe solvent removed
  7. dissolutionThe mixture was dissolved in dichloromethane
  8. filtrationfiltered over silica gel
  9. washThe silica gel was eluted with ethyl acetate
  10. customthe solvent removed under vacuum
  11. additionNext, ethyl ether was added
  12. customthe solids collected under vacuum
  13. washThe solids were washed with ethyl ether
  14. customdried

Sources & evidence

ORD record
ord-85399c4fd7d84d51806ade7f1b97e068
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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