Methyl iodide → tert-butyl (6R,7S)-7-(3,4-dichlorophenyl)-6-(methylamino)-1,4-oxazepane-4-carboxylate

HRID 1022727Notes

Reaction equation

HRID 1022727 reaction equation
[NH2:1][C@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[O:7][CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1.[CH3:24]I>C1COCC1.C(OCC)(=O)C>[Cl:16][C:11]1[CH:10]=[C:9]([C@@H:8]2[O:7][CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3][C@H:2]2[NH:1][CH3:24])[CH:14]=[CH:13][C:12]=1[Cl:15]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 66975508tert-butyl (6R,7S)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 66976611tert-butyl (6R,7S)-7-(3,4-dichlorophenyl)-6-(methylamino)-1,4-oxazepane-4-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (6R,7S)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (150 mg) in THF (4 mL) was added methyl iodide (0.026 ml) at room temperature, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (30 mg).

Workup

  1. washThe diluted solution was washed with distilled water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-de40324e5da84666a0140abdb3d79239
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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