(R)-2-((tert-Butoxycarbonyl)amino)-3-((2-nitrophenyl)amino)propanoic acid → (R)-2-tert-butoxycarbonylamino-3-(2-aminophenylamino)-propi onic acid

HRID 1698770Notes

Reaction equation

HRID 1698770 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H: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]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[C].[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 54512598(R)-2-((tert-Butoxycarbonyl)amino)-3-((2-nitrophenyl)amino)propanoic acid

Product 1

HCID 58595312(R)-2-tert-butoxycarbonylamino-3-(2-aminophenylamino)-propi onic acidYield 80%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-(−)-2-tert-butoxycarbonylamino-3-(2-nitrophenylamino)propionic acid (7.6 g) in tetrahydro-furan (100mL), 10% palladium carbon (1 g) was added, followed by stirring at room temperature for 3 hours under a hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure, whereby (R)-2-tert-butoxycarbonylamino-3-(2-aminophenylamino)-propi onic acid was obtained. It was dissolved in toluene (100 mL). The solution was refluxed overnight. The reaction mixture was allowed to cool down and then concentrated under reduced pressure. The residue was purified by silica gel colomn chromatography (ethyl acetate:n-hexane=1:1), whereby the title compound (5.16 g) was obtained. Yield: 80%.

Workup

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

Sources & evidence

ORD record
ord-2a9a744fa0134cb6a8b2300425381b68
Source dataset
uspto-grants-2002_02
Patent number
US06344452B1

Reaction notes

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