HCID 70183495, compound → HCID 70182935, compound

HRID 1698764Notes

Reaction equation

HRID 1698764 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([NH2:23])([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-])=O)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[C:1]([O:5][C:6]([NH:8][C:9]([NH2:23])([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 70183495HCID 70183495, compound

Product 1

HCID 70182935HCID 70182935, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

(±)-2-tert-Butoxycarbonylamino-3-(2-nitrophenyl)-amin opropionic acid (325 mg) was dissolved in methanol (50 mL), followed by the addition of 10% palladium carbon (50 mg). The resulting mixture was stirred at room temperature for 1 hour under a hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure, whereby (±)-2-tert-butoxycarbonylamino-3-(2-aminophenyl)-aminopropi onic acid was obtained. It was suspended in toluene (30 mL) The suspension was refluxed for 3 hours while removing water by a Dean-Stark extractor. The resultant mixture was concentrated under reduced pressure. After the residue was purified by silica gel colomn chromatography (chloroform:methanol=20:1), diisopropyl ether was added thereto for crystallization. Crystals so precipitated were then collected by filtration, whereby the title compound (210 mg) was obtained. Yield: 76%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3cff3304a4d54e3f8b10cfb0aa8b2569
Source dataset
uspto-grants-2002_02
Patent number
US06344452B1

Reaction notes

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