Methanesulfonic Acid → HCID 24768595, compound

HRID 1716277Notes

Reaction equation

HRID 1716277 reaction equation
C([O:8][N:9]1[CH2:15][C:14]([CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:13][CH2:12][C@@H:11]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:10]1=[O:41])C1C=CC=CC=1.CS(O)(=O)=O>>[Cl:40][C:37]1[CH:36]=[CH:35][C:34]([O:33][C:30]2[CH:31]=[CH:32][C:27]([S:24]([NH:23][C@@H:11]3[CH2:12][CH:13]=[C:14]([CH2:16][N:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)[CH2:15][N:9]([OH:8])[C:10]3=[O:41])(=[O:26])=[O:25])=[CH:28][CH:29]=2)=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 68515875HCID 68515875, compound

Product 1

HCID 24768595HCID 24768595, compoundYield 49.3%

Procedure

To 251 mg of N-(1-Benzyloxy-6-morpholin-4-ylmethyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-chloro-phenoxy)-benzenesulfonamide was added 8 mL of methanesulfonic acid. The reaction was stirred at room temperature for 20 hours, and then the solution was poured over ice. After the ice melted, the aqueous layer was extracted with ethyl ether. The aqueous layer was then neutralized with NaHCO3(s). The aqueous layers were then extracted with dichloromethane three times. The organic layers were then washed with NaCl(aq.) solution, and dried over Na2SO4(s). Filtration and solvent removal was followed by filtration over silica gel and elution with an ethyl acetate methanol mixture (4:1). Solvent removal, dilution with ethyl ether, filtration of the solids and drying gave 105 mg of a beige solid. MS: 1037 (2M+Na), 530 (M+Na), 508 (M+H).

Workup

  1. additionthe solution was poured over ice
  2. extractionthe aqueous layer was extracted with ethyl ether
  3. extractionThe aqueous layers were then extracted with dichloromethane three times
  4. washThe organic layers were then washed with NaCl(aq.) solution
  5. dry with materialdried over Na2SO4(s)
  6. filtrationFiltration and solvent removal
  7. filtrationwas followed by filtration over silica gel and elution with an ethyl acetate methanol mixture (4:1)
  8. customSolvent removal, dilution
  9. filtrationwith ethyl ether, filtration of the solids
  10. customdrying

Sources & evidence

ORD record
ord-b638b181c80548f9920ec20a925a111c
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

Loading…