Ethyl Acetate → HCID 66990706, compound

HRID 454590Notes

Reaction equation

HRID 454590 reaction equation
[CH2:1]([O:8][C:9]1[CH:36]=[CH:35][C:34]([N+:37]([O-])=O)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CO.C(O)(=O)C.[Fe]>[NH2:37][C:34]1[CH:35]=[CH:36][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([CH:33]=1)[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])=[O:12]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 66990211HCID 66990211, compound

Product 1

HCID 66990706HCID 66990706, compoundYield 49.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalyst2×HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Iron powder (43 mg) was added to a solution mixture of tert-butyl 2-(2-(benzyloxy)-5-nitrobenzamido)-4-phenylbenzoate (0.14 g) in methanol (1.4 mL) and acetic acid (1.4 mL), followed by heating to reflux for 1 hour. The reaction mixture was cooled to room temperature, and iron powder (14 mg) was added thereto, followed by heating to reflux for 30 minutes. The reaction mixture was cooled to room temperature, and a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added thereto. The insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 90-50% hexane/ethyl acetate] to obtain 0.065 g of tert-butyl 2-(5-amino-2-(benzyloxy)benzamido)-4-phenylbenzoate as a yellow solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 1 hour
  3. temperatureby heating
  4. temperatureto reflux for 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe insoluble substance was removed by filtration
  7. customThe organic layer was separated
  8. washwashed with a saturated aqueous solution of sodium bicarbonate
  9. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 90-50% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-185dd8b1c00149b9871b625514f9136e
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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