Benzene, 2-fluoro-4-methyl-1-nitro- → (S)-3-(5-Methyl-2-nitro-phenylamino)-5-phenyl-pentanoic acid ethyl ester

HRID 1747292Notes

Reaction equation

HRID 1747292 reaction equation
F[C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Cl.[CH2:13]([O:15][C:16](=[O:28])[CH2:17][C@@H:18]([NH2:27])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:14].CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:13]([O:15][C:16](=[O:28])[CH2:17][C@@H:18]([NH:27][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH3:14]

Participants

6

Reactant 3

HCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 81531DiisopropylethylamineHCID 67359326(S)-3-Amino-5-phenyl-pentanoic acid ethyl ester hydrochloride

Product 1

HCID 59497545(S)-3-(5-Methyl-2-nitro-phenylamino)-5-phenyl-pentanoic acid ethyl esterYield 56.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-Fluoro-4-nitrotoluene (0.7 g, 4.5 mmol) in DMF (5 mL) were added (S)-3-Amino-5-phenyl-pentanoic acid ethyl ester hydrochloride (1.2 g, 4.5 mmol) and DIPEA (1.6 g, 9.0 mmol). The reaction mixture was stirred at room temperature for 48 h. 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 an orange solid. The resulting residue was Purified by silica gel prep TLC using 4:1 Hexanes:ethyl acetate as an eluent to afford 0.9 g of the desired product.

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. concentrationconcentrated
  4. customto afford an orange solid
  5. customThe resulting residue was Purified by silica gel prep TLC

Sources & evidence

ORD record
ord-272b25c17459421388c7594fe89901f5
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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