Methanesulfonic Acid → 4-(4-Chloro-phenoxy)-N-(1-hydroxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-benzenesulfonamide

HRID 1716270Notes

Reaction equation

HRID 1716270 reaction equation
C([O:8][N:9]1[CH2:15][CH:14]=[CH:13][CH2:12][C@@H:11]([NH:16][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:34])C1C=CC=CC=1.CS(O)(=O)=O>O>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([O:26][C:23]2[CH:22]=[CH:21][C:20]([S:17]([NH:16][C@@H:11]3[CH2:12][CH:13]=[CH:14][CH2:15][N:9]([OH:8])[C:10]3=[O:34])(=[O:18])=[O:19])=[CH:25][CH:24]=2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 68512178N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-chloro-phenoxy)-benzenesulfonamide

Product 1

HCID 547524464-(4-Chloro-phenoxy)-N-(1-hydroxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 257 mg of N-(1-benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-chloro-phenoxy)-benzenesulfonamide from Step E was added 6 mL of methane sulfonic acid. The reaction was stirred at room temperature for 16 hours. The reaction was poured over ice, and 50 mL of H2O was added. The resulting solids were filtered, washed with H2O (4 times), and dried. The solids were dissolved in ethyl acetate, and Hexanes was added after solvent reduction under vacuum. The resulting solids were filtered and washed with Hexanes (3 times), followed by drying. Obtained was 195 mg of a white solid (Compound 1). MS: 839 (2M+Na), 431 (M+Na), 409 (M+H).

Workup

  1. additionwas added
  2. filtrationThe resulting solids were filtered
  3. washwashed with H2O (4 times)
  4. customdried
  5. dissolutionThe solids were dissolved in ethyl acetate
  6. additionHexanes was added after solvent reduction under vacuum
  7. filtrationThe resulting solids were filtered
  8. washwashed with Hexanes (3 times)
  9. customby drying
  10. customObtained

Sources & evidence

ORD record
ord-da28e2bdb24b489dadca1e95960f9d15
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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