2,5-Difluoronitrobenzene → 2-Dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-3-methyl-butyric acid

HRID 1348640Notes

Reaction equation

HRID 1348640 reaction equation
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:9]([C:13]([OH:16])([CH3:15])[CH3:14])[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1[N+:32]([O-:34])=[O:33].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>O1CCCC1>[CH2:17]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]([C:13]([O:16][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1[N+:32]([O-:34])=[O:33])([CH3:15])[CH3:14])[C:10]([OH:12])=[O:11])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 677672,5-DifluoronitrobenzeneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 210914032-Dibenzylamino-3-hydroxy-3-methyl-butyric acid

Product 1

HCID 210914022-Dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-3-methyl-butyric acidYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.41 g (4.51 mmol) 2-dibenzylamino-3-hydroxy-3-methyl-butyric acid and 0.54 ml (4.95 mmol) 2,5-difluoronitrobenzene in 46 ml tetrahydrofuran were treated at 0° C. with 19.8 ml (9.9 mmol) potassium bis(trimethylsilyl)amide (0.5 M in toluene). The solution was stirred overnight at room temperature and was then poured on ice/water. Extraction with ethylacetate and chromatography on silicagel with diethylether/heptane (30:70 to 75:25) and yielded 0.40 g (20%) 2-dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-3-methyl-butyric acid as yellow solid, MS m/e (%): 453.4 (M+H+, 100).

Workup

  1. additionwas then poured on ice/water
  2. extractionExtraction with ethylacetate and chromatography on silicagel with diethylether/heptane (30:70 to 75:25)

Sources & evidence

ORD record
ord-18e52d13d69b4b3e9f80af3385f030b9
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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