Methyl iodide → HCID 90281977, compound

HRID 1497544Notes

Reaction equation

HRID 1497544 reaction equation
[C:1]([O:5][C:6](=[O:41])[CH2:7][N:8]([CH2:28][C:29]1[CH:30]=[C:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[S:32][CH:33]=1)[CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[CH:15][C:14]=1[Cl:27])=[O:11])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:45].[Cl-].[NH4+]>O1CCCC1.O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:41])[CH2:7][N:8]([CH2:28][C:29]1[CH:30]=[C:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[S:32][CH:33]=1)[CH2:9][C:10]([N:12]([C:13]1[CH:18]=[CH:17][C:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[CH:15][C:14]=1[Cl:27])[CH3:45])=[O:11])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 90282335HCID 90282335, compound

Product 1

HCID 90281977HCID 90281977, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-{[(2-tert-butoxy-2-oxoethyl){2-[(4-{[tert-butyl(dimethyl)silyl]oxy}-2-chlorophenyl)amino]-2-oxoethyl}amino]methyl}thiophene-2-carboxylate (375 mg) in tetrahydrofuran (7.50 mL) was added 55% sodium hydride (25.2 mg) under ice-cooling, followed by stirring at room temperature for 30 minutes. Iodomethane (0.187 mL) was added thereto at room temperature, followed by stirring at room temperature for 2 hours. To the reaction mixture was added ethyl acetate, and water and a saturated aqueous ammonium chloride solution was added thereto under ice-cooling. The organic layer was extracted, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 4-{[(2-tert-butoxy-2-oxoethyl) {2-[(4-{[tert-butyl(dimethyl)silyl]oxy}-2-chlorophenyl)(methyl)amino]-2-oxoethyl}amino]methyl}thiophene-2-carboxylate (209 mg).

Workup

  1. temperaturecooling
  2. customat room temperature
  3. stirringby stirring at room temperature for 2 hours
  4. temperatureunder ice-cooling
  5. extractionThe organic layer was extracted
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2706ae045b074134adabac176055961c
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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