HCID 15490830, compound → HCID 15490831, compound

HRID 1979287Notes

Reaction equation

HRID 1979287 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[O:11]=[C:10]1[NH:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][CH2:13][CH:9]1[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

4

Reactant 1

HCID 15490830HCID 15490830, compound

Product 1

HCID 15490831HCID 15490831, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-tert-Butoxycarbonylamino-3-(2-nitrophenyl)aminopropionic acid (325 mg) was dissolved in methanol (50 ml). 10% Palladium carbon (50 mg) was added thereto, and the mixture was stirred at room temperature for one hour under hydrogen atmosphere. The resultant mixture was filtrated, and the filtrate was concentrated under reduced pressure to thereby obtain 2-tert-butoxycarbonylamino-3-(2-aminophenyl)aminopropionic acid, which was suspended in toluene (30 ml), and the mixture was refluxed with heat by use of a Dean-Stark so as to remove water for 3 hours. The resultant mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=20:1). Diisopropyl ether was added thereto for crystallization, and the mixture was filtrated to thereby obtain 210 mg of the title compound (yield: 76%).

Workup

  1. filtrationThe resultant mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure to thereby obtain 2-tert-butoxycarbonylamino-3-(2-aminophenyl)aminopropionic acid, which
  3. temperaturethe mixture was refluxed
  4. temperaturewith heat by use of a Dean-Stark so as
  5. customto remove water for 3 hours
  6. concentrationThe resultant mixture was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
  8. additionDiisopropyl ether was added
  9. customfor crystallization
  10. filtrationthe mixture was filtrated

Sources & evidence

ORD record
ord-56ea86f7fc9444c0a76934f8f3fd7179
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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