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Iodoethane → Tert-butyl 4-(3-((tert-butoxycarbonyl)(ethyl)amino)phenyl)-2-nitrobenzoate

HRID 454519
Notes
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Reaction equation

HRID 454519 reaction equation
[H-].[Na+].O1CC[CH2:5][CH2:4]1.[C:8]([O:12][C:13]([NH:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[C:24]([N+:35]([O-:37])=[O:36])[CH:23]=2)[CH:19]=[CH:20][CH:21]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(I)C>C(OCC)C.O.CN(C)C=O>[C:8]([O:12][C:13]([N:15]([CH2:4][CH3:5])[C:16]1[CH:17]=[C:18]([C:22]2[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[C:24]([N+:35]([O-:37])=[O:36])[CH:23]=2)[CH:19]=[CH:20][CH:21]=1)=[O:14])([CH3:9])([CH3:10])[CH3:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6340Iodoethane2×HCID 8028TetrahydrofuranHCID 24758Sodium hydride2×HCID 66990036Tert-butyl 4-(3-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoate

Product 1

HCID 66990682Tert-butyl 4-(3-((tert-butoxycarbonyl)(ethyl)amino)phenyl)-2-nitrobenzoate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 3283Diethyl EtherSolvent
HCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, 60% sodium hydride (43 mg) was added to a tetrahydrofuran (5.0 mL) solution of tert-butyl 4-(3-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoate (0.30 g), followed by stirring at the same temperature for 20 minutes. Ethyl iodide (0.087 mL) was added to the reaction mixture under ice-cooling, followed by stirring at the same temperature for 30 minutes and then at room temperature for 2 hours and 40 minutes. N,N-Dimethylformamide (3.0 mL) was added to the reaction mixture at room temperature, and then 60% sodium hydride (14 mg) and ethyl iodide (0.058 mL) were sequentially added thereto under ice-cooling, followed by stirring at room temperature for 1 hour. Water and diethyl ether were added to the reaction mixture, and the organic layer was separated, washed with a 10% aqueous solution of citric acid and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography [eluent: 85-60% hexane/ethyl acetate] to obtain 0.16 g of tert-butyl 4-(3-((tert-butoxycarbonyl)(ethyl)amino)phenyl)-2-nitrobenzoate as a colorless oily substance.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturecooling
  3. stirringby stirring at the same temperature for 30 minutes
  4. waitat room temperature for 2 hours
  5. custom40 minutes
  6. temperatureunder ice-cooling
  7. stirringby stirring at room temperature for 1 hour
  8. customthe organic layer was separated
  9. washwashed with a 10% aqueous solution of citric acid
  10. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe obtained residue was purified by silica gel column chromatography [eluent: 85-60% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-f2215a8c8f974bdc896a86e68d103e48
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492582B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes