Methyl iodide → HCID 91072451, compound

HRID 1942558Notes

Reaction equation

HRID 1942558 reaction equation
[CH2:1]([N:8]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:9][CH2:10][N:11]1[C:16]2[CH:17]=[C:18]([C:22]([N:24]([CH2:45][CH3:46])[C@@H:25]3[C@@H:30]([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=4)[CH2:29][CH2:28][N:27]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:26]3)=[O:23])[C:19]([F:21])=[CH:20][C:15]=2[O:14][C:13]([CH3:48])([CH3:47])[C:12]1=[O:49])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:57](=O)([O-])[O-].[K+].[K+].CI.[Cl-].[NH4+]>C(#N)C>[CH2:1]([N:8]([CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[CH2:9][CH2:10][N:11]1[C:16]2[CH:17]=[C:18]([C:22]([N:24]([CH2:45][CH3:46])[C@@H:25]3[C@@H:30]([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:57])[CH:32]=4)[CH2:29][CH2:28][N:27]([C:38]([O:40][C:41]([CH3:44])([CH3:42])[CH3:43])=[O:39])[CH2:26]3)=[O:23])[C:19]([F:21])=[CH:20][C:15]=2[O:14][C:13]([CH3:47])([CH3:48])[C:12]1=[O:49])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 91103747HCID 91103747, compound

Product 1

HCID 91072451HCID 91072451, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl (rac.)-(3R,4R)-3-[({4-[2-(dibenzylamino)ethyl]-7-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl}carbonyl)(ethyl)amino]-4-(3-hydroxyphenyl)piperidine-1-carboxylate (82.5 mg) was dissolved in acetonitrile (2 ml), and thereto were added potassium carbonate (29.8 mg) and methyl iodide (13.4 μl), and the mixture was refluxed for 3 hours. The reaction solution was cooled, and thereto was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=2/1) to give the title compound (68.6 mg).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperatureThe reaction solution was cooled
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-781f80d6b68b4fcfba4dd8598c605420
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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