Hydrochloric Acid → HCID 44209914, compound

HRID 1492503Notes

Reaction equation

HRID 1492503 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:39])[NH:11][CH2:12][C:13]([N:15]([CH:22]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=2)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[CH:6]=[CH:7][CH:8]=1.C(O)C.C(=O)(O)[O-].[Na+]>[Fe].O>[NH2:36][C:33]1[CH:34]=[CH:35][C:30]([CH:22]([N:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:13](=[O:14])[CH2:12][NH:11][C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH3:2])[CH:4]=2)=[O:39])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 86748332HCID 86748332, compound

Product 1

HCID 44209914HCID 44209914, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

0.68 g of iron powder and 0.5 cm3 of concentrated hydrochloric acid are added to a suspension of 2.1 g of tert-butyl (RS)-2-{2-[3-(3methylphenyl)ureido]-N-phenylacetamido}-2-(4-nitrophenyl)acetate in 40 cm3 of a mixture of ethanol and water (50/50 by volume) heated under reflux. The reaction mixture is kept under reflux for 4 hours and after cooling it is rendered alkaline to pH 8 using a saturated aqueous sodium bicarbonate solution. The insoluble product is removed by filtration and the filtrate is extracted with 3 times 100 cm3 of dichloromethane. The organic extracts are washed with twice 100 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The oily residue obtained is purified by chromatography on 100 g of silica (0.04-0.063 mm) contained in a column 3 cm in diameter [eluent: methanol/dichloromethane (1/99 by volume)], using an excess pressure of 40 kPa of nitrogen and collecting 10-cm3 fractions. Fractions 8 to 14 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from isopropyl ether, 0.8 g of tert-butyl (RS)-2-(4-aminophenyl)-2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetate melting at 108° C. is obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperatureunder reflux for 4 hours
  4. temperatureafter cooling it
  5. customThe insoluble product is removed by filtration
  6. extractionthe filtrate is extracted with 3 times 100 cm3 of dichloromethane
  7. washThe organic extracts are washed with twice 100 cm3 of water
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  10. customThe oily residue obtained
  11. customis purified by chromatography on 100 g of silica (0.04-0.063 mm)
  12. customcollecting 10-cm3 fractions
  13. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  14. customAfter recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-0f0bc1c111854bf3aa074c28e119fff4
Source dataset
uspto-grants-1994_12
Patent number
US05374656

Reaction notes

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