Acetic Acid → HCID 86636261, compound

HRID 541794Notes

Reaction equation

HRID 541794 reaction equation
[I:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].CO.C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.[Fe]>[NH2:18][C:16]1[CH:15]=[CH:14][C:3]([CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[C:2]([I:1])[CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 10340Sodium CarbonateHCID 86636262HCID 86636262, compound

Product 1

HCID 86636261HCID 86636261, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Into the reaction was added tert-butyl (2-iodo-4-nitrobenzyl)methylcarbamate (4.90 g, 12.5 mmol), methanol (85 mL), acetic acid (14.2 mL) and iron (4.19 g, 75.0 mmol) powder. The reaction solution was heated at 50° C. for 1.5 h. After cooling to room temperature, the reaction solution was diluted with ethyl acetate and a saturated sodium carbonate solution. The reaction mixture was filtered through a pad of celite and washed with EtOAc. The aqueous layer was extracted with ethyl acetate once. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography to yield the desired product (4.10 g, 91%). LCMS calculated for C13H191N2O2Na (M+H)+: m/z=385.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washwashed with EtOAc
  4. extractionThe aqueous layer was extracted with ethyl acetate once
  5. washThe combined organic solutions were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-7ca37c63485142b78db43a1a1327d57f
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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