Ethanol → (2 R)-2-(N-(1,1-dimethylethoxycarbonyl)amino)-5-(5-methyl-2-nitrophenylamino)pentanoic acid

HRID 2379458Notes

Reaction equation

HRID 2379458 reaction equation
[C:1]([NH:8][C@@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH2:11][CH2:12][NH2:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][C:19]=1C.[OH-].[Na+].[CH2:30](O)C>>[CH3:5][C:4]([CH3:7])([O:3][C:1]([NH:8][C@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:18]1[CH:19]=[C:20]([CH3:30])[CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:14]([OH:16])=[O:15])=[O:2])[CH3:6]

Participants

5

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 7019681(R)-5-Amino-2-((tert-butoxycarbonyl)amino)pentanoic acidHCID 134709572-Fluoro-1-methyl-3-nitrobenzene

Product 1

HCID 18656137(2 R)-2-(N-(1,1-dimethylethoxycarbonyl)amino)-5-(5-methyl-2-nitrophenylamino)pentanoic acidYield 61%

Procedure

To 696 mg (3.0 mmol) of Boc-D-Ornithine (as a 1M solution in ethanol) was added 551.5 mg (3.30 mmol) of 2-fluoro-3-nitrotoluene and 3 ml (3 mmol) of 1N sodium hydroxide. The reaction was heated to reflux for 24 hours. The reaction was concentrated/n vacuo. The product was purified by flash chromatography with acetonitrile/acetic acid/water 6/1/1. The product (620 mg, 61% yield) was obtained was a yellow oil. mp>258° C. (dec.). MS (FAB) M/Z: 268 (M+H). 1H NMR (300 MHz, CDCl3) δ: 1.7-2.0 (m, 4H), 2.1 (s, 9H), 2.45 (s, 3H), 3.40 (t, 2H), 4.00 (t, 1H), 6.60 (td, 1H), 7.10 (dd, 1H), 8.00 (dd, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 24 hours
  3. concentrationThe reaction was concentrated/n vacuo
  4. customThe product was purified by flash chromatography with acetonitrile/acetic acid/water 6/1/1

Sources & evidence

ORD record
ord-a1ce11a8dde9431f8bd16f55a152acf0
Source dataset
uspto-grants-1994_11
Patent number
US05362747

Reaction notes

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