Potassium Iodide → HCID 66975454, compound

HRID 1022735Notes

Reaction equation

HRID 1022735 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][C@H:7]1[C@H:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([F:21])[CH:15]=2)[O:12][CH2:11][CH2:10][N:9]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:8]1)=[O:4].Cl.[F:30][C:31]1([F:37])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C@@H:13]2[O:12][CH2:11][CH2:10][N:9]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:8][C@H:7]2[CH2:6][NH:5][C:3](=[O:4])[CH2:2][N:34]2[CH2:35][CH2:36][C:31]([F:37])([F:30])[CH2:32][CH2:33]2)=[CH:15][C:16]=1[F:21]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 66975195HCID 66975195, compound

Product 1

HCID 66975454HCID 66975454, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl (6R,7R)-6-{[(chloroacetyl)amino]methyl}-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate (130 mg), 4,4-difluoropiperidine monohydrochloride (94 mg) and potassium iodide (9.91 mg) in THF (3.0 mL) was added potassium carbonate (248 mg), and the mixture was stirred at 60° C. overnight. To the reaction mixture was added distilled water, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (133 mg).

Workup

  1. additionTo the reaction mixture was added
  2. distillationdistilled water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with distilled water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-13557f0b01bc49c88e5e7ec57e349208
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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