Hydrochloric Acid → HCID 9906437, compound

HRID 726698Notes

Reaction equation

HRID 726698 reaction equation
C(NC(C)C)(C)C.CC(C)([O-])C.[K+].[F:14][CH:15]1[C:21](=[O:22])[C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N:18]([S:27]([C:30]2[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH2:17][CH2:16]1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:47])(=O)=O)=CC=1.Cl>O1CCCC1.CCCCCC>[F:14][C:15]1([F:47])[C:21](=[O:22])[C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N:18]([S:27]([C:30]2[CH:31]=[CH:32][C:33]([CH3:34])=[CH:35][CH:36]=2)(=[O:29])=[O:28])[CH2:17][CH2:16]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 588007N-FluorobenzenesulfonimideHCID 108065444-Fluoro-1-tosyl-3,4-dihydro-1H-benzo[B]azepin-5(2H)-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 9906437HCID 9906437, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To 300 ml of tetrahydrofuran solution containing 2.62 g of diisopropylamine and 2.91 g of potassium t-butoxide was added dropwise 16.2 ml of 1.6N n-hexane solution of n-butyllithilum at -78° C., followed by 30 minutes of stirring at -78° C. To this reaction solution was added 70 ml of tetrahydrofuran solution containing 7.2 g of 4-fluoro-1-tosyl-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one, followed by 1 hour of stirring at -78° C. The reaction solution was mixed with 70 ml of tetrahydrofuran solution containing 10.22 g of N-fluorobenzenesulfonimide, and the mixture was stirred for 2 hours at -78° C. and then for 1 hour at room temperature. The reaction solution was mixed with 500 ml of 0.1N hydrochloric acid aqueous solution and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with 10% sodium thiosulfate, 1N sodium hydroxide and saturated sodium chloride aqueous solution in that order and dried over anhydrous magnesium sulfate, subsequently evaporating the solvent. The resulting residue was applied to silica gel column chromatography, which was eluted with a mixed solvent of n-hexane and ethyl acetate (4:1, v/v) to obtain 2.31 g of 4,4-difluoro-1-tosyl-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one.

Workup

  1. waitfollowed by 1 hour
  2. stirringof stirring at -78° C
  3. stirringthe mixture was stirred for 2 hours at -78° C.
  4. waitfor 1 hour at room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe resulting organic layer was washed with 10% sodium thiosulfate, 1N sodium hydroxide and saturated sodium chloride aqueous solution in that order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customsubsequently evaporating the solvent
  9. washwas eluted with a mixed solvent of n-hexane and ethyl acetate (4:1

Sources & evidence

ORD record
ord-05f1437cec464e8ab33c6d10d9f57b85
Source dataset
uspto-grants-1998_01
Patent number
US05710150

Reaction notes

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