Water → HCID 66975904, compound

HRID 1022795Notes

Reaction equation

HRID 1022795 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:16]I)[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].[C:31]([NH:34][CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)(=[O:33])[CH3:32].O>CN(C=O)C>[C:31]([NH:34][CH:35]1[CH2:40][CH2:39][N:38]([CH2:16][CH:15]2[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH:9]2[C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:37][CH2:36]1)(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14451564-AcetamidopiperidineHCID 66976424HCID 66976424, compound

Product 1

HCID 66975904HCID 66975904, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-(iodomethyl)-1,4-oxazepane-4-carboxylate (300 mg) in DMF (5 mL) were added potassium carbonate (260 mg) and 4-acetamidopiperidine (130 mg), and the mixture was stirred at 80° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (190 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a1eb4af6f80446a4af6423a56dcb28f5
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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