1-Fluoro-2-nitrobenzene → (S)-2-(2-Nitro-phenylamino)-propionic acid tert-butyl ester

HRID 1747385Notes

Reaction equation

HRID 1747385 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][C@H:12]([NH2:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].Cl.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[C:16]([O:15][C:13](=[O:14])[C@@H:12]([NH:20][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[CH3:11])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 11275390tert-Butyl alaninate hydrochloride

Product 1

HCID 59497415(S)-2-(2-Nitro-phenylamino)-propionic acid tert-butyl esterYield 95.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-fluoronitrobenzene (1.0 g, 7.09 mmol) in DMF (5 mL) were added H-ALA-OTBU HCl (2.6 g, 14.2 mmol) and DIPEA (2.5 mL, 14.2 mmol). The reaction mixture was stirred at room temperature over the weekend. The reaction mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was then dried over Na2SO4 and concentrated to afford 1.8 g (95%) of the desired product as orange oil. The resulting residue was used for the next reaction without further purification.

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f91a952027234bcdbc3e3d02fcdcf62a
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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