Potassium Iodide → HCID 66975885, compound

HRID 1022757Notes

Reaction equation

HRID 1022757 reaction equation
Br[C:2](F)(F)[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(OC(C)(C)C)=O)[CH2:8]1)=[O:4].[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.[I-].[K+].C(=O)([O-])[O-:39].[K+].[K+]>C1COCC1>[ClH:20].[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C@@H:13]2[O:12][CH2:11][CH2:10][NH:9][CH2:8][C@H:7]2[CH2:6][NH:5][C:3](=[O:4])[C:2](=[O:39])[N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:15][C:16]=1[F:21]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 66976327HCID 66976327, compound

Product 1

HCID 66975885HCID 66975885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl (6R,7R)-6-({[bromo(difluoro)acetyl]amino}methyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate (176 mg), pyrrolidine (0.085 mL) and potassium iodide (11.3 mg) in THF (3.4 ml) was added potassium carbonate (282 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). The obtained residue was subjected to an operation similar to that of Example 38, step E to give the title compound (11.7 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-568f95a6e8a144589272e2f9cd4d2128
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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