Methanesulfonic Acid → 4-(4-chlorophenoxy)-N-[(6R)-1-hydroxy-7-oxo-5,6-dihydro-2H-azepin-6-yl]-N-(2-morpholin-4-ylethyl)benzenesulfonamide

HRID 1716274Notes

Reaction equation

HRID 1716274 reaction equation
C([O:8][N:9]1[CH2:15][CH:14]=[CH:13][CH2:12][C@@H:11]([N:16]([CH2:34][CH2:35][N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[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:42])C1C=CC=CC=1.CS(O)(=O)=O>>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([O:26][C:23]2[CH:24]=[CH:25][C:20]([S:17]([N:16]([C@@H:11]3[CH2:12][CH:13]=[CH:14][CH2:15][N:9]([OH:8])[C:10]3=[O:42])[CH2:34][CH2:35][N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)(=[O:19])=[O:18])=[CH:21][CH:22]=2)=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 68516379HCID 68516379, compound

Product 1

HCID 547524454-(4-chlorophenoxy)-N-[(6R)-1-hydroxy-7-oxo-5,6-dihydro-2H-azepin-6-yl]-N-(2-morpholin-4-ylethyl)benzenesulfonamideYield 106.1%

Procedure

To a solution of 2.83 g of N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-chloro-phenoxy)-N-(2-morpholin-4-yl-ethyl)-benzenesulfonamide from Step B was added 35 mL of methane sulfonic acid. The reaction was stirred at room temperature for 20 hours. The reaction was then poured over ice. The aqueous layer was extracted with 100 mL of ethyl ether twice, followed by extraction of the aqueous layer with dichloromethane (4 times). The dichloromethane layers were combined and dried over Na2SO4(s). The liquids were filtered off, and solvent removal gave a light yellow film. Dilution with ethyl ether, filtration of the resulting solids, and washing with ethyl ether and hexanes followed by drying gave 2.56 g of an orange solid. MS: 522 (M+H).

Workup

  1. additionThe reaction was then poured over ice
  2. extractionThe aqueous layer was extracted with 100 mL of ethyl ether twice
  3. extractionfollowed by extraction of the aqueous layer with dichloromethane (4 times)
  4. dry with materialdried over Na2SO4(s)
  5. filtrationThe liquids were filtered off
  6. customsolvent removal
  7. customgave a light yellow film
  8. filtrationDilution with ethyl ether, filtration of the resulting solids
  9. washwashing with ethyl ether and hexanes
  10. customby drying

Sources & evidence

ORD record
ord-b6628174bb894133beac2e953ef46724
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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